November 13, 2003

You hate me.

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October 30, 2003

Dear Sheila,
Help! It’s the day before Halloween and I still don’t have a costume. Any last minute ideas that might get the boys' blood pumping?
Cute Costume Seeker

Dear CCS,
Ah, Halloween. An opportunity for the kids to go out late, walk around with their friends, cover themselves in gobs of makeup, wear things they wouldn’t normally wear in public, and see the inside of strange people’s houses, all with the single goal of getting some candy.

It’s no different for single women. Halloween, as we all know, is really just a ruse for us refined, J.Crew-wearing ladies to experience the freedom and fun of dressing like the slut-bags we normally hate for a night. This is part of what makes Halloween such a prime hook-up fest.

But Halloween also gives even the most shy, tongue-tied, sackless fool out there an “in”. A girl dressed as a catholic school girl, struggling to buy a drink in a crowded bar, is never going to be as approachable as she is right at that moment. Unless, of course, you’re dressed like a priest, in which case school girls aren't your thing.

With that in mind, here are a couple of last minute costume ideas to bring out the slut in you:

1). Girl Scout
What you need: Your old girl scout outfit, sash and beret included
Slut factor: 7 (depending on how plump of a girl scout you were and how tight it is now)
Allure: Every guy will want your thin mint.
Downside: You’ll get plenty of offers to earn your handjob badge.

2). Cheerleader
What you need: A cheerleader outfit, some pom-poms
Slut factor: 8
Allure: “Give me a P-E-D-O-P-H-I-L-I-A”
Downside: “What’s that spell? SKETCHY GUYS!”

3) Bridesmaid
What you need: Your ugliest bridesmaid dress (everyone has one)
Slut factor: 2 (4 if you get really drunk and hit the dancefloor)
Allure: Every guy knows a bridesmaid wants to hook-up.
Downside: Scariest costume at the bar, by far

5) Cowgirl
What you need: Cowboy hat, tight jeans, flannel shirt tied in a knot at the waist, chaps and a lasso
Slut factor: 9
Allure: Helloooo? Chaps and a lasso?
Downside: You’ll ALWAYS have to be on top.

6) Football player
What you need: Tight white pants, some smudge under the eyes, and a helmet
Slut factor: 5
Allure: Get to ask cute boys to “hit the showers.”
Downside: May be forced to keep the helmet on if he has a headboard.

7) Frat boy
What you need: Dirty baseball cap, an Abercrombie shirt, some khakis.
Slut factor: 4
Allure: You’ll remind him of his carefree college days.
Downside: Which were probably spent screwing his pledge brothers.


October 27, 2003

Dear Sheila,
In regards to your last column, I felt it was my duty as a short guy to inform you that not all short guys have small penises. There’s absolutely no correlation between height and dick size. On behalf of short guys everywhere, you’re a moron.

Dear DICK,
Even though I don’t really care for your attitude, I have to admit that you have a point - using other physical attributes to forecast a man’s penis size is rarely accurate. Height, hands, shoe size, torso length – none of these old wives tales work (damn old wives – this was the least they could do for us young single girls). For the most part, there really has been no way of telling if a guy is sporting a Bic or a Buick without getting your hands, and maybe your sheets, a little dirty.

That is, until now. Based upon years of my own painstaking and sometimes painful field work, I’ve created my own methodology that can help you determine how big a guy is to within a quarter of an inch, just on the first date.

It’s quite an easy formula, really. Just start at the average (6”), and as the date goes on, add or subtract length (in increments of an inch) based on few common first date things:

1.) Picks you up at your apartment instead of meeting you at the restaurant = +1/8”
This shows confidence, and confidence is good. It also means you don’t have to pay for the cab, so we’re going to give him the benefit of the doubt.

2.) Brings flowers = +1/16”
Flowers say romance. Flowers say chivalry. Flowers say girth.

3.) Immediately puts napkin on lap upon being seated = - 1/8”
You might think this is good manners. It’s actually a “penis duvet,” which means the little fella gets cold easily. Poor circulation could lead to limpness issues.

4.) Cell phone rings during date = -1/8”
Attempts to look popular is really just a muffled cry for help from a little weiner.

5.) Orders beer = +1/8"
(Orders a light beer = +0”; orders an Amstel Light = -1/4”)

6.) Excuses himself to use the rest room before the second drink = -1/8”
A bladder the size of a walnut does nay bode well.

7.) Orders oysters = -1/4”
Dork. Does this even work?

8.) Orders a bottle of wine to share = +1/8”
Which coincidentally happens to be the least expensive bottle on the menu = -1/16”
Whiffs the wine cork = -1/8” (God I hate that. He can't tell what good wine is, just like he can't use his unit.)

9.) Asks about your family = -1/16”
Alas, the sensitive ones are sensitive because they have small penises.

10.) God he’s saying some stupid things = +1/8”
The penis is hogging the blood flow to his brain.

Of course, if he's rich, it really doesn't matter.


October 16, 2003

Dear Sheila,
I’m a 5’1” girl, and just recently started dating this guy who’s like 5’6”. We got to talking the other night, and he told me that he only dates girls who are 5’3” or shorter. So now I’m asking myself: is he dating me because he really likes me, or because he has a short girl fetish?
Petite and Neurotic

Dear PAN,
He’s dating you because his pack-of-Certs-sized cock looks like a Snapple bottle in your little elfin hands.

And yes, I just got back from the corner deli.


October 9, 2003

Dear Sheila,
I’ve been dating this one girl for about two months and we’ve been having sex regularly but she absolutely refuses to go down on me. She says that our relationship “isn’t quite ready for that yet.” What does this mean? Can you please help translate this to MaleSpeak for me?
Awaiting the BJ

Dear AtBJ,
There are two types of girls in the world: those that believe oral sex always comes before regular sex, and those that don’t.

Personally, I am a strict adherent to the traditional hook-up orifice sequence: manual (kind of an orifice), oral, vaginal, and lastly, on special occasions, anal.

What can I say. Call me old fashioned.

The question is really which act does the girl you’re with consider to be more intimate. I have many friends that consider blowing a guy to be a far more intimate act than regular sex. Which is, when you really think about it, probably true. Unless you’re one of the 7 women in the Western hemisphere that uses a condom during oral sex (and I know that’s awful and so unsafe of us, but its true), you’re discovering how bitter his baby gravy is. That’s pretty personal. After the third date, you may not even know his parent’s names. Do you really need to know he likes asparagus?

But I’m set in my ways, and still believe regular sex to be the more intimate of the two acts. Maybe it has to do with the guy actually being inside me. Or maybe it’s because I can really look him in the eye. Or maybe it’s because I’m sharing pleasure instead of giving pleasure, and I don’t feel someone has more or less power than the other.

But that’s just me, and every girl is different. If she feels that giving head is something she’s not ready for, then it’s something she’s not ready for. When the time is right, and your relationship has evolved, I’m sure she’ll be all about smoking the blue-veined Havana.

Of course, you may have to come to terms with a more solemn and brutal and horrible truth: she just doesn’t like it, and you're never getting it.


September 27, 2003

Dear Sheila,
After reading the “Mazel Tov!” comic series on engagement rings, I thought you would be the perfect person to ask: what’s the minimum size ring, in terms of carats, I have to buy for my girlfriend? I know everyone says that it's not the size that counts, and that she’d be happy with anything I give her if she’s in love with me, but give me the honest truth.
Nervous Ring Buyer

Dear NRB,
You’re absolutely right - it doesn’t matter how big it is, it’s all about love, and if she’s in love, she’ll be happy with whatever, blah blah blah.

That being said, the absolute minimum size to truly express real love is 1 and a quarter carats. Think of it like lobster. The minimum size you can order in most restaurants is a 1 and a quarter pound lobster. I don't even think they sell one pound lobsters. It’s illegal in most states. You have to, and should, throw it back. But you also don’t want to buy one that's too big, like a 3 pounder because they’re just too chewy at that size.

Just kidding. Chewy is fine.


September 25, 2003

Before we go into this week’s question, I just want to apologize for missing last week’s. I got a lot of nasty notes from a few of you, and not to get all sentimental and crap, but it really warmed my heart. All you really need to know is that writing this column is one of the highlights of my week, and if I miss it, it’s because something, or someone, really important came up, (both figuratively and literally - wink wink). But I’ll catch up, and do an extra column. So check back here sometime this weekend for the make-up. Now, onto this week’s question…


Dear Sheila,
My girlfriend never wants to sleep at my apartment. As a result, we always end up staying at her place. Doesn’t there need to be some balance? Should we implement a split-time schedule?
Sick of Her Apartment

Dear SoHA,
There are ultimately four possible reasons why your girlfriend doesn’t want to sleep at your place:

1. Your apartment’s a shithole.
The fact that single guy’s have disgusting apartments really isn’t news to anyone, and it's easily the most common cause of women not willing to commit to the away game. But odds are, you most likely have no idea how revoltingly funky your apartment really is. It probably has that Single Guy Apartment smell (an odor mélange of the gym, decaying rotisserie chicken, and feet), and your bed is probably covered in Single Guy Apartment sheets (25 thread count polyester blend, last washed during the Clinton administration, and festooned with a nice pattern of various discharge stains). I think they should just sell sheets for single guys that already come with asymmetrical off-white stains on them so they can at least try to camouflage how infrequently they wash: “New this fall from Wamsutta – Man Butter.”

2. She doesn’t have all her necessary equipment at your place.
If you’re at the point of doing the mid-week sleep over, odds are she’s going to have to shower at your apartment at some point. Back to point #1, your shower is probably more of a hydroponic mold farm than an acceptable cleaning area. But even if she’s willing to step into the terrarium you call a tub, she still doesn’t have all her critical shower and post-shower paraphernalia. All women, you see, have a set routine of shampoos, conditioners, lotions, moisturizers, scrubs, powders, muds and balms that are customized for each part of our bodies. The whole process really needs its own column. Just know that your Pert Plus and Irish Spring aren’t going to cut it.

3. Acoustic limitations of a co-habitational lifestyle.
No girl wants your two shithead roommates to hear her having sex.

4. She’s not that into you.
I bring this up only because, despite reasons #1 -#3, girls do put up with all this crap. I sometimes find it astonishing what we will deal with if we like a guy. We’ll shower in slime, sleep in crusty filth, and put up with burping, farting roommates if not being with you is worse. Sometimes, finding a guy that gives you sparkles is worth trudging through a little grime.

And you all clean up once we've got you whipped anyway.


September 18, 2003

It appears Sheila is skipping her duties this week. She was supposed to catch-up on the column this weekend, but instead spent the weekend sunning herself in Central Park, enjoying what may very well have been the last nice weekend of the year. She'll be back this Thursday though. So come back then.


September 11, 2003

Dear Sheila,
A friend told me that sperm is really fattening. Am I going to have to spend another hour a week on the stairmaster, just for giving a BJ?
A Moment On The Lips

If this is true, I think we just may have cracked the reason behind America’s obesity epidemic. Or the Freshman Fifteen, anyway. But as any guy will tell you, there really just aren’t enough girls out there who swallow to possibly account for a nation of fatties. So anecdotally speaking, my guess is that sperm isn’t fattening. But here at Sheila’s Male Bag, we pride ourselves on doing the due diligence necessary to help any girl avoid an unnecessary hour of stairmaster hell.

According to the Research Guide to Bodily Fluids (Paul Spinard, 1994), the average man produces 3.5mL of semen per ejaculate, whose nutritional value is not only incredibly healthy, but also diet friendly! Take a look:

  • Less than 1 calorie (just like a Diet Coke)
  • 150 mg. protein (great for all you Atkins freaks)
  • 11 mg carbohydrates (for that little boost of energy, like a power bar)
  • 6 mg. fat (the good kind, I’m sure, like in guacamole)
  • 7% US RDA potassium (ironically, that’s the same as if you sucked a banana)
  • 3% US RDA of both copper and zinc (its practically a Centrum!)

So cut out the smoothies and wheatgrass, you health freaks, and get out there and play the pink oboe. Frankly, I’m surprised Nantucket Nectars or Fresh Samantha hasn’t come out with a “Soy and Sperm” shake at this point that you can pick up at your local grocer. Maybe Vitamin Water, whose products are all named after their benefit (“Determination”, “Energy”, “Leadership”) will come out with “Gag.”

Because even though its healthy, its not exactly a carmel frapp.


September 4, 2003

Dear Sheila,
Is it safe to spread Nutella on all body parts? I mean, my boyfriend sometimes likes to apply it before he goes down on me, and I’m not sure how thorough he is at getting it off - it’s not like I take a shower after every time we hook up. I know this seems like a weird question, but I just don’t want some weird chocolate infection.
Nutella Nookie

Dear NN,
For those of you who don’t know what it is, Nutella is a delicious chocolate-hazelnut creamy spread, usually applied to toast, not labia.

As much fun as it sounds, and as big of a proponent as I am of doing whatever necessary to encourage a guy to give good head, I found out that this culinary technique of yours is actually a pretty bad idea. Dr. Charles Moser of gives a few tips when considering turning your vagina into a buffet:

"The vagina is cautious territory for food play. Sugar is off limits in the vagina. Even a little can encourage bad bacteria and yeast growth, and a lot does something nasty called 'osmotic pull' that causes real damage in there. That includes sugary substances such as fruit, sweetened whipped cream, soda or sugary drinks and liqueurs. Don't blow air into the vagina, as this can lead to fatal embolism. It's rare, but not unheard of. That probably means no Perrier douches, as much fun as this concept may sound. Alcohol, especially hard alcohol, is also a bad idea up in here."

No sweets?! No whipped cream?! If that’s not a total buzz kill, I don’t know what is. But you shouldn’t let this ruin your oral fun.

How does your boyfriend feel about hummus?


August 28, 2003

Dear Sheila,
I’m in my twenties, and constantly seem to be going for guys that I know will create drama in my life. Either they have a girlfriend, or they’re not Jewish, or they live in a different country. The one constant is that all my relationships are emotional roller coasters: all ups and down, never just normal. I just seem to gravitate to guys that I know will present some kind of challenge and the relationship won’t be easy. Why can’t I just be happy with a nice, normal guy?
Drama Queen

Dear DQ,
To use an overplayed marketing term, you’re an “X-treme Dater.” You need the rush and burst of adrenaline that comes from thrills, danger and the risk of getting hurt. And if you’re anything like me, you probably despise sweating of any kind, so you get your drama from dating instead of mountain biking.

And what’s wrong with that? Why are you concerned? What’s wrong with emotional roller coasters? Is it distracting you from more important things like “client sales presentations” and “timesheets”? Now’s the time to date for drama, DQ! Be your own Melrose Place! Date guys with girlfriends! Date a married guy at least once! Hell, even date a non-Jew if it suits your fancy - see the elusive uncircumsized penis!

In fact, if thrills, danger and the risk of getting hurt are the conditions necessary for an event to qualify as an extreme sport, then I think “X-treme Dating” should be part of the next ESPN Games. If Puerto Rican cliff diving can count as an official X-treme sport, I don’t see why “I’m dating a guitar player with two illegitimate kids and serious communication issues” isn’t. You have to be pretty stupid to get involved in either.

But that’s what being young is all about – doing stupid shit. Because now’s when you can still get away with it.

In fact, I would say the potential for drama should be your ONLY dating prerequisite at this point in your life. Date people because you want to. Date people because they turn you on. Date people because they’ll be a good story. Date people because you can. Date people because you have the rest of your life to sit at home on a Friday, order in Chinese, rent a movie and have missionary sex.

People are always saying how your twenties are the time to experiment, and they’re right. Travel, try out different careers, spend frivolously, bungee-jump...and date people that aren’t good for you.

It’s the only way you’ll find out who is.


August 21, 2003

Dear Sheila,
I dated this guy for like 3 years, broke up with him about a year ago, and I haven't seen him since. I've now been dating another guy for about six months, who I really like. Out of the blue, I decided to go into my ex-boyfriend’s Ofoto account online (I still had the password), which is where he keeps all his digital photos. I don't know why I did this, I just did. So I saw all these old pictures of us from when we dated and it was weird. And there were also some new photos: 1). He looked really hot. 2) There were pics of him with other girls. Not doing anything dirty, but definitely drunk and having fun. And one of the girls was a girl who I know had a crush on him for awhile.

My question is: Why did I do this to myself? I’m suddenly thinking I might have made a mistake. How can I stop thinking about past?
Brooding Snooper

Dear BS,
One of the best things about ex-boyfriends, especially ones you were really close to, is knowing their old passwords. There was a time when I would log into one of my ex-boyfriend’s Hotmail account once a week. He had told me the password once, over dinner, but I don’t think he expected me to remember it (it could have been in hieroglyphics - of course I was going to remember it). So after we broke up, I would occasionally read his email.

Yes, I know, it’s a violation of privacy. Yes, it’s morally reprehensible. That being said, I felt justified because even though the break-up was mutual, towards the end of the relationship he had pulled that whole “distant” thing, which I hate. So screw him. It’s also his fault for telling me his password in the first place, and then never changing it. (Note to everyone out there – change your password every so often – you never know who’s reading). I had to see what he was saying about me.

What I learned was that guys’ emails suck. He didn’t have the diatribes that girls write to each other after a break-up. Where was the post-break-up analysis? Where were the detailed, transcribed accounts of our final conversation? He had things from friends that were like: “Sorry to hear about the break-up. But I’m really sorry that Warner got injured. Your fantasy team just got killed, dude.”

Months later, as I was cleaning out my inbox, I found a bunch of old emails from him. They were the cute funny ones that guys write when they’ve just started dating and are actually trying to get a girl to like them. So it got me thinking about him, which led to me logging into his account. As I was reading a few emails, I found an exchange between him and a girl I didn’t know. It was obvious from the exchange that they had just started dating. The biggest clue to this was that HE WAS USING THE SAME EXACT EMAILS HE SENT TO ME. That’s right, he was repurposing our cute little email exchanges to get some other girl into bed.

My point here is that as time passes, we always forget the bad and remember the good. We remember picnics at the beach, inside jokes, and tender kisses. We forget all the times he farted under the covers and pulled the sheets over our head. Or when his aim was off and he “accidentally” tried for anal sex. But the bad – whatever it was that caused the relationship to end with that person – is still there.

It's never as good then as we think it was now.


August 14, 2003

Dear Sheila,
This is going to sound weird, but it turns me on to squeeze my boyfriend's zits. As soon as I see one, I want to tear into it. Not only do I do get a rush out of the actual act, but I then really want to have sex. Is this weird?
Pimple Popping Pleasure

Dear PPP,
You know, there’s are more than a few sex columnists out there that will tell you there’s no such thing as a weird fetish and that anything done between two consenting adults is perfectly normal.

They’re high.

You see, PPP, I am a firm believer that some things are, objectively and without debate, just bizarre, and the idea of them makes me want to vomit. The range of freaky shit people do behind closed doors never ceases to amaze me, and usually I’m just glad I haven’t encountered it in my own field work.

All that being said, I have to admit that I LOVE popping guys’ zits myself. It just doesn’t turn me on. I can sympathize with your lust for hot white man cream, but not when it refers to pus. That’s the only thing I think is weird. I know more than a few girls who enjoy tending their man’s skin, but it doesn’t bust Dolores out in a sweat.

So is it weird? Unequivocally yes. But take comfort in the fact that it only rates about a “2” on the Sheila Weird Scale – there are a lot more freakier people out there than you.


August 11, 2003

Two things:

1). Sheila's Male Bag has officially moved to Thursdays.

2). Bitch missed this past week's column, extending her vacation by an extra week. Our resident diva WILL, however, be back this Thursday. See you then.


July 16, 2003

Dear Sheila,
This is going to sound weird, but I’m deathly afraid of an erect penis. I’m okay if I don’t see it, but once I’ve seen it, I want nothing to do with it. Not only is this completely bizarre, but I think my boyfriend thinks it’s him, even though I’ve always had this problem. Is there anything I can do? Do you think I need to see a shrink? Help!
Fear of Phallus

Dear FOP,
I’ve heard of being annoyed by an erect penis, but never scared of one. So I did a little research and found that your condition has an official name – Medorthophobia, which literally means “fear of an erect penis.” Astoundingly, there was no term “fear of a flaccid penis,” which I think is the far more scary of the manhood states. My only advice is to try and spend as much time around erect penises as possible, and hopefully you’ll overcome this. Maybe try interning for a urologist or something. But truly, you have my deepest sympathies, and I would latch onto any help, professional or otherwise, you can find.

Yes your condition is bizarre, but the fact is we all have strange fears. Some say it’s our quirks that make us all unique. I say it’s our fears. Although the names aren’t official (as I made them up), below is a quick list of some of mine that I think should become a part of every psychologist’s vocabulary:

Gagophobia - Fear of eating a black JuJu fruit accidentally during the movies.

Someonetookitphobia - Fear that someone will steal the your towel while you’re in the shower in the gym.

4pm-Stankophobia - Fear that throwing out your lunch in your own waste basket will make your whole office smell by the end of the day.

OhfortheloveofGodophobia - Fear of dating someone who’s all too comfortable not closing the door when they shit.

Everyfreakingflavorphobia - Fear of never being able to find just plain Snapple iced tea, yet all the weird flavor amalgamations are there.

Hello?Notreallyfriendsaphobia - Fear of getting asked to be a bridesmaid of someone you know you won’t ask to be one of yours.

Noonelikesyouaphobia - Fear of sending out an Evite and having no one reply.

Youbastardophobia - Fear of cubic zirconia.

Circulationproblemaphobia - Fear of forgetting to bring a sweater with you when going to the movies.

Firedophobia - Fear of not properly hanging up the speakerphone after a conversation with your client.

Futzyphobia - Fear of farting when someone goes down on you.

Futzedonphobia - Fear of getting farted on when going down on someone.

I’lljustsitbythepoolaphobia - Fear that your vacation in the Bahamas will coincide with your period.


July 9, 2003

Dear Sheila,
I was wondering if you could help me decide whether someone is gay. This New York guy friend of mine, in the past, has regaled stories about how he slept with all these girls, how much he loves to scam for girls, and how much he loves to go clubbing. However, I never see him with any women. Or men, for that matter. Plus, he dresses somewhat nicely. Despite all this, he's very quiet and shy when it comes to bigger groups. And, he seems more sensitive than other guys and sometimes acts more feminine that I do.

I honestly can't get a read on this guy. At this point, he seems almost asexual to me. Are there other clues I should be looking for? I don't know this person well enough to just ask in a straightforward manner. Help!
Staring at Ambiguity

Dear SAA,
This is the problem with being a single girl in New York: as far as I can tell, 50% of all the single guys in New York are gay. They are also disproportionately the best looking guys in the city, probably because they all go to the gym at 6am for a vigorous half hour run on the treadmill, followed by an even more vigorous 15 minutes of sperm burping in the steam room.

With what little information you gave me, there are three options for categorizing for your boy here:
1). He’s gay
2). He’s a straight “metrosexual” – a straight guy that acts gayish
3). He’s British

Assuming he doesn’t have an accent, you have to ask yourself a few questions:

  • Are all his shirts and sweaters one size too small, and disproportionately “ribbed”?
  • If you asked him “if you were an ice cream, what flavor ice cream would you be?” does he comment how fattening ice cream is or say "But ugh, Phish food is to DIE for!"
  • Does he have a George Hamilton-level tan in January?
  • Is Dep gel, as far as hair products go, a bit too “Wal-Mart” for him?
  • Does he have more than 6 pairs of jeans…and not just blue ones?
  • Does he think a Yuengling is the name of the cute new Asian guy in accounting?

Did you answer “yes” to at least one of the above?

Unfortunately, it won’t help you.

Fact is, in New York, its high near impossible to tell a tubesteak tarzan from a carpet muncher. Their personas have completely blurred together in this weird Kenneth Cole/non-comedogenic moisturizer haze.

Of course, you could just offer to take him out for a few green apple martini’s (which you know he’ll be up for), insist on bringing him back to your place (so you can show him the pictures of your nephew he’s been dying to see), and accidentally slip your tongue around his freshly apricot-balmed lips.

If he can’t stay because the “Knicks are playing the Cubs,” well, at least you have a new friend who you can make you great techno mix CDs for the gym.


July 2, 2003

Sorry, no Sheila this week. Some sort of apple pucker incident. She'll be back next week though, so click the link above and send her your questions.


June 25, 2003

Dear Sheila,
I went on a first date the other night with a guy who is nice, decent looking, and not working at McDonalds. (Obviously a catch!) He has already asked me out on a second date. The problem is I am not sure we have that spark, that indefinable something that makes you want to finish dinner fast so you can move on to the kiss. In fact, I am not sure I want to kiss this guy at all. So should I waste his time and mine on a second date?
To Spark or Not To Spark

You obviously haven’t read all my columns, TSONTS. My very first one, waaaaay back on Feb 5, talked about the Kiss Rule: “If you can sit in your room and imagine yourself kissing this guy, then it’s OK, because he still has a shot. If the thought of kissing him is unappealing, then it’s probably not a good idea. And if the idea of giving him sloppy wet head makes you gag (well, more than usual) then you really shouldn’t do it.”

I think that rule still holds. But the fact that this is second question I’ve had on this topic hints at a larger issue: why do we women constantly consider dating guys we may not be that attracted to?

Two words: The Drama.

Dating is something to do. It’s that feeling of having someone chase after you and knowing that they want you. It’s the anticipation of having something, sometimes anything, to do after work with someone of some potential and wondering where the night might lead. It’s getting a little “Days of Our Lives” in the nights of our lives.

Fact is, I don’t have enough information to know if “the spark” was really missing, or if the guy just looked like a less attractive cousin of Steve Buscemi and would never even make it into your consideration set, regardless of any multipliers his personality might eventually give his overall score.

If you’re at least somewhat not sure about this, and you think this guy has a fraction of potential, and you have no other guys in the hopper, and you don’t have a TiVo, I boldly suggest going on a second date. Maybe the lighting was off. Maybe he had a long day at work. Maybe his dog had just died. Maybe he ate an entire bag of olestra potato chips at lunch and was completely paranoid his ass might start leaking. I don’t know. Regardless, sometimes “the spark” just needs the right conditions.

Just make sure they include an apple martini (or three) this time.


June 18, 2003

Dear Sheila,
I’m debating on whether to attend a friend’s wedding or not. She’s a good friend, and the reply card is due at the end of this week. I’m allowed to bring a date, but I’m not currently dating anyone who I’d feel comfortable asking. And to make matters worst, ALL of my friends that are going are bringing boyfriends or husbands. So there I’ll be, stranded at the singles table…or worse, the only single girl at a table full of married people. What do you think, Sheila? Should I even go to this wedding?
Desperately Hating Weddings

Dear DHW,
I absolutely understand your predicament. But as a single girl who’s attended many a wedding on her own, I can attest that things aren’t nearly as bad as they seem. Opportunity abounds at these nuptial events, as the single guys are on the prowl looking for a lass “weakened” by all the romantic goings-on. Leverage that persona correctly, and you can guarantee yourself a good time.

There are, however, times when being the single girl at a wedding is akin to being the tampon in the Tiffany crystal punchbowl.

So to help you out, I devised a little score card to help you determine if this wedding offers opportunity or misery. Any plus score is good; any negative score is bad. As long as your total score comes out positive in the end, I say it’s a go.

So without further ado, here’s Sheila’s SINGLE GIRL’S SCORE CARD FOR ATTENDING A FRIEND’S WEDDING:

1. The bride is…
…a really good friend. [+10]
…that you really haven’t talked to in awhile. [+1]
...because the conversations suck, and she’s one of those people who you don’t really like anymore but you’ve been “friends” forever, and you’ve just been too much of a wuss to break-up with her. [-5]
…but at least the she didn’t put you in her bridal party and make you buy the $350 puffy fuscia vomit stain she called a bride’s maids dress. [+10]

2. The group of friends that are going are…
…good friends from college or high school that you want to see. [+10]
…friends from college or high school you could care less if you see. [-1]
…like that Stephanie Blankstein bitch from 11th grade. [-5]
…who has reportedly put on 30 pounds since having her three illegitimate children. [+25]

3. It’s confirmed. You’ll be sitting at the singles table…
…not knowing anyone else there. [-15]
…but there’ll be a 4:1 ratio of single guys to single girls. [+5]
…the other single girls are the groom’s cheese-thighed, backne-covered cousins from Wisconsin. [+10]
…and early scouting reports on the guys from the bride reveal they’re all cute doctors. [+15]
…gynecologists, to be exact. [-20]

4. The Ex-Factor: will any ex-boyfriends…
…be attending? [-1]
…which is ok, because you’ve been going to the gym regularly, and have a great new dress that really accentuates your chest, which you know he loves [+5]
…and you would definitely consider hooking up with him again [+10]
…except he’s bringing his new fiancé [-25]
…who he starting dating 2 weeks after you broke-up [-30]
…and got engaged to after dating for a total of three months, even though you two dated for three and a half years [-100]

And there you have it: an undisputable decision-making methodology.

What was your score, DHW?


June 11, 2003

Dear Sheila,
After you've gone on a successful first date with someone in another city, what's the best way to follow up? It seems awkward and pressure-filled to ask someone to travel (far enough that he would have to stay overnight) for a second date, or does it?
Stuck In The Midwest

Dear SITM,
First of all, SITM, no one is “stuck” in the Midwest. "Stuck" is wearing a short skirt and trying to get off a leather couch in your grandmother’s humid, non-air conditioned Florida condo. "Stuck" is giving a hand job with a cheap moisturizer that turns into an industrial adhesive after 5 strokes.

You, my dear, just don’t sound happy out there, especially if you’re dating people from other cities. And who can blame you? Just thinking about living life as a single girl in the bread basket of America gives me a yeast infection.

But if you’re actually going to try and ship this guy in for a cross-country booty call, you need to go on a few more “virtual dates” between now and when he comes so you both feel comfortable with not only the invite itself, but the second date sleepover (i.e. – you don’t feel like a slut when you sleep with him on the “official” second date.).

For example, if you invite a guy that you’ve been out with once to come stay with you, and there’s a plane flight involved, that plane flight counts as like two additional (“virtual”) dates. So you’re now on your third date. Odds are, you’ve also been doing quite a bit of emailing before his trip as well – that’s like another two dates. And if you’ve been talking on the phone every once in awhile, that counts as at least another two or three dates. If you sometimes call to tell each other good-night (in like a cutesy way, where you talk lying in bed while watching the same TV show and ask if the other one’s fallen asleep yet, blah blah), that’s huge. That counts as like four or five additional dates.

So by the time your official second date rolls around when you actually see this person for real, you could conceivably be on like your 20th date.

Then, the only thing that’s awkward and pressure-filled over the weekend is doggy style.


June 4, 2003

Dear Sheila,
The first time you hook-up with a guy, do you think it’s better to spend the night at your place or his?
Location Location Location

Dear LLL,
I always prefer the away game. Three reasons:

1. Clutter Factor. If I’m not planning on having a sleepover that night, and a guy unexpectedly comes back to my place, odds are my room has a raging and embarrassing breakout of “Outfit Selection Mess” – a state of cotton-blended chaos were almost every outfit I own is strewn across the room from trying them all on before I went out. Guys just don’t acknowledge or appreciate the Mess for its role in making you look your hottest.

2. Dirty Guy Factor. I can deal with some guy’s hairy nakedness on me, but NOT on my 300 thread count Calvin Klein duvet. Big no no.

3. Evacuation Factor. I like being able to ditch the guy when I want to. There’s nothing worse than getting stuck with a snorer in some disgustingly hot, non-air circulating room, lying wide-awake in a cramped, shitty little full-sized bed, completely parched and fantasizing about Gatorade.

Also, I hate having someone spend the night at my place and then leaving conspicuously early. It’s OK if I do it, but if I like him, I wouldn’t mind a little morning lingering. There’s nothing worse than hearing “I’d love to stay, but I really have to get to work early.” And it’s 5:30am. Now I've got a shitty start to my day because I’ve spent the rest of the night and morning going through every possible scenario and minute detail of the night to rationalize why he might have left.

So really, it comes down to a control issue. Yeah, going back to his place means you have to do the “Walk of Shame Past Your Doorman Who Now Thinks You’re a Ho.” And yeah, you might have to deal with the mental high-fives from this guy’s roommates in the morning, a black-skirted, high-heeled piece of evidence that their boy got some that night.

But at least you don’t have to spend your Sunday washing man-butter out of your sheets.


May 28, 2003

Dear Sheila,
I read your letter to "Planning the Week" last week and thought it was great. So I have a first date question of my own: do you think you should really be yourself on a first date, as everyone says you should, or do you think it’s better to hold off the "real you" until you’ve gotten to know that person better?
Getting To Know Me

Dear GTKM,
The only girls who can really get away with truly being themselves on a first date are gourmet-cooking, SportsCenter-loving, bisexual contortionists. The rest of us need to hold off a bit before illuminating all the nooks and crannies of our true selves on a first date.

I am all about being yourself, and I don’t think any guy is ever worth not being yourself for. But some people (guys and girls) take this "being yourself" thing a little too far a little too soon, and decide to bring along their 29-piece collection of Louis Vuitton psychological baggage with them whenever they meet up with someone for drinks for the first time.

Look, we all have our little quirks and neurosis. These are the wonderful things that make us the delectable, adorable things that we are. The problem is that these quirks and neurosis are really only cute after someone’s decided if they like you. Otherwise, they’re annoying as shit.

So when I say "don’t be yourself" on a first date, I really mean "just be your less freaky qualities for now." Or as my mother liked to say, "just show him your cream, honey." (Cute, right? Do you know how many guys in high school got to third until I figured out what she meant?)

Again, this doesn’t mean you shouldn't be who you are, or show your true personality. Just reserve your weirdest thoughts, peculiarities and imperfections until AFTER you’ve gotten to know each other a bit better…and you’ve made his toes curl from a mind-numbing bj.

After that, I promise he’ll think your little gas issue is cute as a button.


May 21, 2003

Dear Sheila,
What’s the best night of the week for a first date? I met this guy last week and I’m trying to figure out what’s the best night to go out with him. What do you think?
Planning the Week

Dear PTW,
Although each day has its strengths and weaknesses, there is one key guideline to use when picking a day: MAKE SURE YOU CAN GET WASTED THAT NIGHT.

95% of all first dates are “just drinks”…and a lot of them. Some guys may offer to meet you for “coffee.” These men have low sperm counts, and should be avoided should you ever be looking to have children rather than import them

You always want to make sure you pick a night you can get a little tipsy because if you like him, you want to be flirty and fun. If you don’t like him, you want to be wasted to keep from fixating on the size of his pores. Regardless, under no circumstances do you want to be sober.

So with the drinking guideline understood, here’s my first date rating for each day of the week:

Sunday – Absolute Worst
Unless his last name is Savagewood, no first date is worth giving up Sunday night HBO. And who wants to drink on a Sunday.

Monday/Tuesday – Almost the Worst
Monday’s are for things you want to get out the way so you don’t spend the whole week thinking and dwelling on them, like trips to the gyno. Also, on a first date, you don’t yet know if this guy’s worth starting out the work week hungover. If he sucks, not only did you waste a night, but now you’re feeling like shit the next day.

What can I say, every girl has her metric of male acceptability. Elaine had “SpongeWorthy,” I have “HungoverWorthy.”

Wednesday – Best
Ah, Hump Day. The bulk of the work week is done, and having a few cosmos is sounding pretty good. And, if the date goes well, it opens the door for the possibility of a weekend rendezvous. See, on a Wednesday, even if you like the guy and you’re drunk, there’s no way you’re going back to his place. That’s just slutty. But if the date goes well, and he asks you out for that Saturday, there’s a distinct possibility of some heavy petting and awkward drunk button removal over the weekend.

So really, the Wednesday date is for your own protection: not only does it prevent you from doing anything stupid on date #1, it imposes a 72-hour waiting period between dates #1 and #2, so you can make a conscious and deliberate decision on whether or not you’d actually like to do something stupid on date #2. It’s like the dating equivalent of buying a hand-gun.

Thursday – Not the Best, Not the Worst
This used to be Must See TV night, but watching Chandler and Monica has now become as excruciating as hanging out with my real married friends.

Friday/Saturday – Not the Worst, But Pretty Bad
On the plus side, it’s a guaranteed upgrade to a dinner date. If he tries to pull the Friday "just drinks", he’s one cheap bastard, and should be left at the Papaya King where you found him.

Unfortunately, there’s just too many downsides: the pressure, the loss of the “early meeting at work” excuse if you want to bail, and the possibility of waking up at his place with your contacts still in.

See, if a guy asks you out for a Friday or Saturday for your first date, he’s trying pull the first date hook. Now, you may have a firm “no first date hook-up” rule. (Of course you do. We all do.) But accepting the weekend first date, and the drinking that will probably ensue, means the potential for an “isolated lapse” exists. So you might want to indulge and wear one of your good thongs, just in case. Of course, if the guy sucks, you just wasted one of your good thongs, adding insult to injury.

And really, aren’t we all just looking for a date that isn’t a waste of a good thong?


May 14, 2003

Dear Sheila,
This guy I just started dating is having his birthday next week. I’m really into him, but as we’ve only been out like four or five times, I’m not quite sure what I should do for it. Should I get him a gift? What’s the protocol here?
Birthday Too Soon

Dear BTS,
The Premature Birthday. Always an awkward moment early in a relationship, right behind “The Premature Valentine’s Day” and “The Astoundingly-Premature Ejaculation.”

The trick with the Premature Birthday is to look thoughtful, but not too much so. Ideally, your gift is something that has a little cutesy meaning between the two of you, and shows you’re starting to get to know him. But of course, you don’t want to over do it. Go too far, spend too much money or make too much of a production around the whole event and you could easily freak him out.

Let’s go through some example scenarios and their suitability:

Coldplay CD he said he wanted to buy – OK
Personalized mix tape of all the songs you’ve hooked up to so far, plus Cheap Trick’s “The Flame” – Not OK

DVD of a favorite Star Trek movie he mentioned – OK
Learning to sing “Happy Birthday” in Klingon – Not OK

Book the two of you talked about that he’s been wanting to read – OK
Some haiku you’ve written about the various hues of hazel in his eyes – Not OK

A small bottle of his favorite cologne - OK
Little vials from the Angelina Jolie/Billy Bob Thornton collection for wearing each other’s blood around your necks, with yours already filled – Severely not OK

Personally, I always like to go the route of getting a new thong for myself, and then telling him it was for him. It’s a disappointment-proof gift for both of us.

If he’d prefer "The Wrath of Khan" to you in something sexy, it probably wasn’t meant to be.


May 7, 2003

Dear Sheila,
After a first date, should I always give the guy a thank you call the following day? My friends are pretty split. What do you think?
To Thank Or Not To Thank

This is a pivotal decision, but ultimately a very easy one: if you liked the guy after the date, call him and thank him.

The Thank You Call, ultimately, is just giving the guy a confirmation that you liked him, and, were he to ask you out again, you would accept. Remember, dates are really just “I might let you see me naked” interviews, and the Thank You Call is like mentally stripping off your first piece of clothing.

Also, men are idiots, and sometimes this is their only metric for success.

I’ve also found the Thank You Email just as effective, and more subtle, than the call. It's best used if you just met for drinks. You also completely avoid the risk of actually talking to him. See also the “Thank-You-Call-to-His-Home-Phone-at-3pm-When-You-Know-He-Is-At-Work.”

Now, when NOT to call after a first date:

  • If you don’t like him
    Never EVER give a Thank You Call if you KNOW that you don’t like the guy! It doesn’t matter how much money he spent (though we like that), who set you up (even if it was your grandmother), or what he does (orthopedic surgeons excluded, of course). It you thank him with no intention of seeing him again, he’ll be calling you like a telemarketer for the next month until you actually go out with him again.
  • If you went “dutch”
    Of course, if you went dutch on the first date, you should be “re-educated” in an Iraqi Olympic Facility for even considering a second date. Unless you’re interviewing potential sperm donors for you and your lesbian partner, there’s no excuse for this.
  • If there was anything more than some over-the-shirt action
    Thanking someone after dry-humping them is just plain creepy. The thank you is pretty much implied.

Now, many girls think that they should NEVER give a Thank You Call, and that the guy should always thank them. I myself was once one of these girls. And most of the time, if a guy really liked you, odds are he will probably call you regardless of your Thank You Call. But every once in awhile, usually if the date went OK but not great, and you’d both be willing to try a second, some guys might not make the effort, thinking of you as a just an OK date AND a non-thanker.

So as with everything else in the dating world, it comes down to how much you force yourself to put yourself out there.


April 30, 2003

Dear Sheila,
I am having issues dealing with my girlfriend's PMS. It seems like every time the 2nd Tuesday of each month rolls around, I’m subjected to merciless accusations, ridiculous tirades and embarrassing emotional outbursts. Of course, like most guys, I would just chalk this up to normal female behavior, but I am not so sure how normal it is. Obviously, when the little red dot comes around, hormones are raging and whatnot, but I am getting a little tired of girls using the monthly flow as a crutch. You see, I used to have a girlfriend who said that girls can always control their behavior and emotions during a period better than most do. They just feel compelled to unleash hell every time something doesn't go their way... or cry uncontrollably even if it does. So, privy to this little secret of female PMS over-dramatization, should I call my girlfriend on it, and tell her to cut the crap?
Sick of Aunt Flo

Dear SAF,
To quote the Iraqi Information Minister: “Infidel! A thousand curses upon your seed! May Balding and Impotence gnomes visit you in the night and grill your testicles in hell!”

Yes it’s real, dipshit. It’s not the Loch Ness monster or a yeti. I’m not sure who your ex-girlfriend is that informed you otherwise, but she should have her head shaved and be forced to wear a Scarlet Stain on her ass for the rest of her life.

Study after study has shown that hormonal imbalances during menstruation are very real, and bound to produce emotional side affects, the scope of which varies among women. But do you want to know the most conclusive scientific evidence available that proves PMS is real?


I dare you to call her on it. In fact, I think you should wait until she is in the middle of one of her “ridiculous outbursts.” If you think you’re dealing with shit now, you have no idea how many octaves higher that outburst will get. Your testicles will be wedged in a George Foreman grill before you can say “honey, put the knife down.”

If you decide to chicken out (which you will, once you catch the frenzied gleam in her eye when you approach her to chat about it - PMS also allows us to detect when men are about to say something stupid), just learn to live with it. It’s not hard. Just sit there, zip the pie hole, scratch yourself if you’re so inclined, and take whatever tirades come your way.

And I dare you to take it with a smile.


April 23, 2003

Dear Sheila,
I just broke up with my boyfriend this past weekend. I am not particularly broken-hearted but I kind of feel like I should do something to get him out of my system. I am not a big fan of the regular girl responses of cutting off my all hair or eating pints of ice cream while watching cheesy movies. Any suggestions?
Tired of the Tried and True

Dear TTT,
This subject of “Managing the Break-up” really deserves its own book, not just one column. But to properly determine how one should handle the aftermath, we really need to go back and analyze all the details of the break-up itself. As this is usually a pretty thorough interview process, and I’ve got a column due, let’s go with the three you’ve provided so far:
1). Who broke up with whom (You tossed him)
2). How much time has passed (3 – 4 days)
3). How you’re feeling about it (Just dandy)

Based on this, I think you’re a ripe candidate to be flirting with your supermarket deli guy by lunch time today, and giving it up wholesale to just about any guy wearing Drakkar and displaying no obvious drooling disorders by 11:28pm this Friday. One couldn’t fault you for taking this route, and I think it’s far preferable than your current options of getting uglier or fatter, TTT. Remember, regardless of who broke up with whom, the key to the entire break-up is looking better the next time you see this person than when you left them. I cannot overstate the importance of this! Also acceptable is you staying the same while they get less attractive. God forbid you break up with a guy, see him six months later, he looks great and you’re sporting the ugly Felicity cut while packing an extra 10 pounds of Ben and Jerry's tricep fat.

Of course, there are a variety of other conditions that affect how one might conduct themselves in the post-break-up period. Why do we need to consider these other variables? Because for some period of time, you two shared your lives. How deep that joint-life went will have a bearing on how quick and clean a break you can make. Some things to consider:

  • How did he handle it? Was crying/begging involved? Are you getting flowers sent everyday? What’s his psycho/stalking potential?
  • How long had you been dating? Did friends refer to the two of you as one person with one joint-name when planning events (e.g., “Are TomandJessica coming”)?
  • Does he know what and where you bleach?
  • How embedded with the family was he? Had he met the parents? Are you going to have to explain to your grandmother why he’s not coming to Rosh Hashanah this year?
  • What’s the mutual friend situation? Do they have to break-up and picks sides too? Will you need to manage all your future relationships around your mutual friend’s wedding schedules to guarantee you’ve always got a date and not languishing at the singles table?
  • How was the sex? What is your desire for consolation sex/drunk booty calls? What’s his likelihood of trying?
  • Were you ever, at any point, in love with him?

Really, it’s only the last one that matters, because everything else is crappy little administrative details. But to get over someone you were in love with, well, that calls for heavy doses of Time and Friends.

That’s why you never ditch your friends for a guy – it sucks to eat ice cream and watch cheesy movies alone.


April 16, 2003

Dear Sheila,
I have a best friend “with benefits” situation going on. My friend and I, let’s call him “John,” have been best friends for like two years, and recently we started hooking up, as we both just got out of serious relationships. I guess I always liked him a little bit the whole time we were friends, but since we started hooking up, I’m in full blown crush mode. He truly is like the greatest guy ever. The other day, we went out with some friends, heavy drinking ensued, and I at one point spilled my guts, in what was I’m sure a very slurred voice. I don’t recall exactly what I said, but I do vividly remember him not saying anything in response. Nothing. He just kinda looked at me. Then the night quickly ended and we both went home. That was two days ago, and we haven’t spoken since. I don’t want to lose him as a friend, but I also want to know if we have any chance, or if I totally screwed this up.
Drunk Lips Sink Ships

Dear DLSS,
Oh DLSS, DLSS, DLSS, DLSS. Don’t you know that passionate, drunk confessions of love only succeed in Freddie Prinze Jr. movies? And can you believe I just used “succeed” and “Freddie Prinze Jr. movie” in the same sentence? Why did you get greedy? You should have just stuck with the sex, and then pulled that away from him when you wanted him to start becoming serious. That’s the only way you’re going to initiate any kind of “serious” talk. When you pull the sex away, he’ll say:
Him: “What’s wrong? Is there something wrong?”
You: “No, nothing. I just don’t think this is a good idea.”
Him <grasping for pathway to panties>: “Let’s date.”

Well, maybe that’s not exactly how it will go, but I’ve seen it happen before. As far as I can tell, there is some part of guys that, however small, need some sort of challenge when starting a relationship. They need to feel like they were the one who somehow overcame insurmountable odds to date you, almost like they’re in their own little version of “Rocky" with “Eye of the Tiger” playing in the background of their little heads. When a girl let’s a guy know that she likes him, a part of him (and I’m firmly convinced of this, no matter what my male friends say) is thinking “easy game.” And where’s the sport in that? I can’t imagine a tiger feels all that accomplished after killing a retarded, one-eyed gazelle with a limp. Guys like the challenge. Guys NEED the challenge. And as a woman, we should know this at this point.

And yet, why all the fucking games, even with guys we’re friends with and comfortable with? Shouldn’t it be different? Of course it should. But it’s not.

My suggestion? Use “Pre-Tests” to determine his interest and your risk of spilling your guts:
Does he schedule “dates” with you (booty calls not withstanding)? Does he shave before he meets you? Does he walk you home? Does he make bets (that he has every intention of losing) with you where the loser has to buy a dinner? Does he make fun of any potential dates with other guys that you might have? After you hooked-up, did he hang around the next morning? Did he want to go to breakfast? Did he offer to cook breakfast? And the biggie, my “go-to” test: did he go down on you for his breakfast?

But now, back to your Big Question: Can you deal with losing him as a friend? If you can, call him up and bring it up again. Be confident. If you can’t really deal with losing him as a friend, go with the blatant lie. Tell him you were really drunk that night and play it off like nothing happened and you don’t remember a thing. If he remembers and wants to pursue anything, he’ll bring it up.


April 9, 2003

Dear Sheila,
Because of some career issues, my boyfriend and I have just started a long distance relationship. As I want to make sure all his “needs” are taken care of while we’re apart, what’s the best way to initiate phone sex? I’ve never done it, and I’m not even sure if he’ll be into it. Any advice?
First Time Talker

Dear FTT,
This is like asking your mother if she’d like your help with the dishes. His answer, no matter how you broach the subject of phone sex, is going to be an emphatic “Yes.” Why? Because doing the dishes is always more fun with a buddy. It’s a partnership that makes a nightly obligation (his pre-bed “release”) a fun joint-task. You scrub, he’ll dry (usually with a tissue).

Now, as you’ve never done it before, here’s a quick recipe that guarantees a first timer’s phone sex success:
1.) Pour yourself glass of wine
2.) Pour yourself a few more (unless you're a "giggling drunk," then stop - no one likes a giggler during phone sex)
3.) Take a bath
4.) Call the boy from the bath
5.) Tell him you are naked, in a bath, and thinking dirty thoughts of him

Now, as most men are not very intuitive about these things, he may not initiate “the talk” at this point, in which case you might want to try something more assertive and understandable for him, such as the "Honey, the team needs you!" approach….

6). Your vibrator ran out of batteries so you’re “calling in Rivera from the bullpen to finish the game.” You have to use that exact line, even though you may not know what it means, and you may hate sports as much as I do. For dramatic effect, I sometimes flick my electric toothbrush on and off next to the receiver.

Not only will he be monumentally impressed, he will understand his role completely, and the games will, ironically, begin.


April 2, 2003

Dear Sheila,
I can't seem to find a guy I really like. I've been in relationships before but in the last couple of years, it’s just been an array of dates that don't go anywhere. Most of the guys I meet are not on the same track that I am on and so we end up having nothing to talk about. So, about 2 months ago I resorted to online dating. I haven't physically met anyone yet. I email back and forth with a few guys. One of them is really interesting and we always have paragraphs and paragraphs of things to say (not to mention that he's a total hottie). I really like him but I just don't have the balls to meet up with him because I'm afraid it will just end up like all the others. Should I just grow some ovaries and meet up with him? Or should I cancel my membership to the online dating site and get back to the real world?
Online Dating Dilemma

Dear ODD,
Yes, you should cancel your membership to the online dating site and get back to the real world.

And while you’re at it, you should cancel your gym membership, stop shaving your pits, refuse to eat anything that doesn’t have the words “cream,” “fried,” or “General Tsao’s” in the name, start harvesting bed sores between your trunk-like inner thighs, join the “Lonely Twat’s Vibrator of the Month Club” and buy about 30 cats, who will be your only male contact other than the daily pizza boy, and will repay your years of kindness, kibbles, and heavy petting by eating your 300 pound corpse after you die, alone, in your ugly stucco house at the top of the hill that all the school kids are afraid to walk by because it smells like stale urine and gefilte fish.

Or…you can take a risk, give life a spin, at worst have a free martini and a story for the friends, at best get the tingle, the itch, that something that makes you notice when his hand brushes by your arm and wow! you’re genuinely surprised that five hours have gone by so fast and you thank him for a great night, actually meaning it for a change, and for hope for a kiss and get the kiss (gentle, but not too much so) then relive the kiss, ponder its nuances, and wouldn’t it be great see this person again and you hope he doesn’t wait the mandatory two days to call and he calls the next day! and you can’t believe you’re nervous just being on the phone…

Seems worth the risk to me, ODD.


March 26, 2003

Dear Sheila,
I’m thinking about shaving off all my pubic hair as a surprise birthday present for my girlfriend. What do you think?

Dear CBB,
There are two possible reactions from your girlfriend:
1). She’ll be incredibly turned on
2). She’ll puke

For Pukers, the penis is not an attractive thing. It should not be glorified. It should be hidden away from the world, coming out into full view only for special occasions, such as hernia exams.

Those who are turned on (myself included) enjoy the novelty of the whole thing. If you can get past the raw-chicken-skin ugliness of it, it can actually feel quite good. But a word of warning – and I cannot stress this enough – KEEP IT TRIM!

For the love of God man, keep it trim.


March 19, 2003

Dear Sheila,

I am a graduating senior and just got a job offer in NYC for next year. Although I am very excited to move to the city, none of my male friends are going to be there with me, so as of now I have no one to room with. My current girlfriend of two years is also moving to NYC and has suggested we get an apartment together, as she has no girlfriends to room with next year either. I do love her, but I’m just not sure whether or not this is a good idea. What if moving in together too soon ruins what could be a great long-term relationship? What should I do?
Real Estate Pickle

Dear REP,
Here are your two scenarios:

1). The Unconverted One Bedroom
Pros: Think of the rent! As a couple, you can get a real one bedroom and not have to convert it into a Depression Era tenement. And you’ll be saving like $300 - $400 per month! Think of the additional shoes she…I mean, you could buy each month! You’ll be spending every night at each other’s place anyway, so you might as well.

Cons: You and this girl WILL break-up within six months. Eventually you’ll both feel hindered in your respective explorations of your fleeting youths, you’ll start resenting each other, their little quirks will become nauseating, and you’ll be another Justin and Britney, just without the toned bodies, gobs of money, or other people waiting to date you.

2.) Separate Apartments
Pros: A place you can each call your own (i.e. – She doesn’t have to deal with you always shitting and stinking up her bathroom before she showers.)

Cons: You run the risk of getting apartments at opposite ends of the City, making each other geographically undesirable, your relationship strained beyond repair from the 30 minute cross-town commute. In NYC, living more than 20 blocks away from your significant other qualifies a relationship as “long distance”, and hence, will be subject to those same pressures. If you’re below 14th Street and she’s on the Upper East Side, you might as well be dating someone in Guam.

So what’s my advice? Although I’d like to tell you that “if it was meant to be, it doesn’t matter what you choose,” but the fact is, I can’t. I don’t buy that. I think there are many possible love matches out there for everyone, and part of finding The One just comes down to the right timing. If you don't think your schedules are in synch, tell her. You have to live your life, PickleBoy, not hers. Get some nads.

Besides, there’s nothing that pisses me off more than seeing a 22 year-old girl closer to marriage than I am.


March 12, 2003

Dear Sheila,
My girlfriend and I are both seniors in college and have been dating for almost three months. We made separate Spring Break plans months ago before we started going out. So now, while I’m spending the vacation at home with the folks, she is going to Cancun with a bunch of her girlfriends. All my friends tell me that it’s pretty much a guarantee that she’s going to cheat on me while she’s down there. What do you think? Can a girl spend her senior year Spring Break in Cancun and be trusted not to cheat?
Going Insane Here

Dear GIH,
She will not cheat on you.
She will, however, hook-up with other guys that aren’t you.

You see, GIH, hooking up with someone that isn't your significant other on Spring Break just doesn’t count as cheating. To actually cheat, a woman has to have no justifiable logic for her behavior. Luckily, that rarely happens, as we women have a plethora of internal rationales at our disposal to prevent any “Spring Break slip-ups” from officially counting as cheating:

1. “We just started dating.”
A woman will use this when the rules of your relationship have not yet been established.
As men use this crap line all the time, I personally love to use this one whenever convenient.
2. “I’m only young once.”
This is our excuse for trying any variety of new things, be it conch fritters, parasailing, or a 3am beach threesome with two University of Michigan Phi Delts. In my opinion, that’s pretty skanky. But the point is, even that can find a way to not be counted.
3. “I was drunk.”
The Spring Break variation of diplomatic immunity. An untouchable defense.
4. “What happens on Spring Break, stays on Spring Break.”
Unless, of course, it’s herpes. Then you have to count it.
5. “We’re not going to last anyway.”
If she believes you two are "on the way out,” “in the process of breaking up,” or “doesn’t think the relationship is long-term,” this will be the logic of choice. Of course, your actual break-up may not happen for 2 or 3 months, sometimes up to a year, but the point is, you’re not The One, and she knows it, so it’s OK to do another body shot or two off the navel of that hot guy at the bar.
6. “It’s just easier if I don’t tell him.”
Honestly, it’s amazing how hung-up some guys get on this, so really, we don’t tell you for your own good. It would just upset you, and it’s really not worth the hassle of the weeks of fighting, the endless talks, blah blah, just to get the relationship back to where it was pre-Spring Break.

You think you want to know, GIH, but you don’t. So forget she’s there, help mom prune the garden or whatever it you’re doing over the break, and suck it up. It’s your own fault for not going somewhere where she can worry about you.


March 5, 2003

Dear Sheila.

What is your take on best friends hooking up? More specifically, I have a best friend we will call Bob. Well, Bob and I have been best friends for about 4 years and all of a sudden we started hooking up. This has been happening for the past 2 months now but we are still best friends and will never date as boyfriend/girlfriend…at least not now. So, we are just having fun and really both of us are having a great time. Because he is not committing himself to me (although he really hasn’t done more than kiss another girl since it has started) does that make me slutty? I mean, I feel like I deserve a guy who committs himself fully to me - but on the other hand, if I can't find that right now and I have something that is great and lots of fun, is that okay???

Baffled Best Friend

Dear BBF,
To answer your two questions (I’m paraphrasing):
1). “Does that make me slutty”? – Yes.
2). “Is it ok to hook-up with a guy just for fun if you feel like you deserve better?” – Yes, just realize you’re being slutty.

Being slutty or not is all about who’s having sex with whom. In this case, he’s banging you. He’s the Banger.

You are being banged. You are the Bangee.

To determine who is having sex with whom, we have to look at the terms of the agreement, and then how you feel about those terms. If you had asked the same question, but left out the part about how you felt you “deserve more” (aka – “want more”), I’d say the two of you were just banging each other - two Bangers in the night, in a mutually understood joint-banging relationship, with no sluttiness factor involved. But since you’re having questions about whether this is OK or not, implying that you “want” more, which insinuates you probably kind of like the guy, well, you’re hooking up with no "hand."

You, my dear, are the Bangee. The alter boy. The Gimp.

I guess my only advice is: doing what you want and being happy with it is the least slutty, most empowering thing a woman can do. Stay true to that, and you’ll always sleep soundly.

The Banger always does.


February 26, 2003

Dear Sheila,
I’m a 27 year old, vibrant young professional woman. Against my better judgment, I hooked up this past weekend with a 24 year old. The problem is that I think I may legitimately like him. So here’s the question: when can an older woman date a younger guy? Could it ever turn into something serious, or is destined to just be a one time slip up, something a girl does just for fun?
Dabbling with Forbidden Fruit

Dear DFF,
This is a tricky problem. Luckily, it seems like we caught it before any real damage was done.

Let me start by saying that the one-time slip up with a younger guy is perfectly acceptable. It’s a nice little self-indulgence. They seem to be everywhere nowadays, and only getting cuter. As my mother used to say, if you spend enough time in the bakery, you’re going to lick the cream out of the cannoli at some point. You shouldn’t do it everyday, but every once in awhile can’t hurt. 9 times out of 10, though, you should just forget about it immediately after it happens.

For that 1 time out of 10, though, when you're actually considering something “more,” here are some general criteria that I use when evaluating a young buck’s long-term potential:
1) Has a decent career. I.e., he makes enough money to take you out on the type of date a 27 year old should be taken out on. You’re not going to Brother Jimmy’s BBQ Bait Shack for rib tips and fishbowls on a Saturday night. At least not sober.
2) Refrains from bar PDA. Making out in public at 27 is for skanks and people who have to get their hook-ups in before they scurry back over the bridge or tunnel from which they came. PDA at your stage, outside of Ibiza, is a no no.
3) Integrates well with your social scene. Not only that, but he can actually carry a conversation beyond just regaling the crowd with tales of his past drunken idiocy. This seems to be the crux of most 24 year old male conversations. Any stories that also entail some type of urination “mishap” are considered a nonnegotiable deal-breaker.
4) And lastly, The Hat Rule. If you see him, ever, wearing a bent, rotting, stained, white baseball cap - the kind that usually leaves some kind of residual discharge on whatever it touches – drop him like your third fork at a restaurant with a hot waiter. The hat is unacceptable under any circumstances, even in Boston.

But the real issue comes down to maturity and “timelines.” He’s just stepped off the boat, straight from undergrad-boot camp, a wide-eyed and naïve young private, still full of ideals and testosterone, and probably going commando more often than not from lack of clean boxers. You’ve already done more than a few tours of duty in the dating jungle. You’re not the grizzled old veteran in the platoon yet, but you don’t want to be either. You've got to be careful you’re not the oat field for his sowing, leading you on til you’re 30 and then dumping you, leaving you stranded on the frontier of middle age, a land practically devoid of available single men in your demographic, while time has left you looking like Willem Dafoe in….well, in anything – Willem Dafoe always looks like crap.

Remember – dating is a war, not a battle. Pick your fights wisely.


February 19, 2003

Dear Sheila,
I’m a 26 year old single female and have been going out with this one guy for like three weeks. He is absolutely incredible! We’ve been on like four dates, and each one has been more amazing than the one before. Even when we’re not out together, we talk on the phone for hours, telling each other everything and sharing our heart’s deepest wants and desires. On our last date, we went to this incredibly romantic Italian restaurant in the Village, had a few glasses of wine, and wound up going back to his place for the first time and doing everything but sleeping together. Even that was perfect. But then suddenly, almost overnight, he became somewhat distant, and hasn’t been returning my calls. Do you think something happened at work that he’s embarrassed to share with me? Or maybe something terrible has happened in his family that he’s scared to tell me about? I want him to know that I’m with him and that he doesn’t have to face this horrible tragedy alone. Any idea what painful ordeal could make a man pull away from something that was so good, so perfect, and so right?
Aching In Heaven

Dear AIH,
You give bad head.



February 12, 2003

Dear Sheila,
This weekend is Valentine’s Day, and I HATE spending Valentine’s Day alone. I’m single, and almost all my friends are in serious relationships and are going out for romantic, sex-filled evenings with their significant others. As I don’t want to spend the night watching “CSI: Miami,” I’m looking for alternative plans. Any suggestions? Should I go out for a wild, girls-night out on the town?

Dear WAV,
Ah yes, Valentine’s Day. One’s feelings on this particular holiday all depend on one’s current dating status. As I am, yet again, single this year, I of course find myself in the “Valentine’s Day Sucks” camp. Being “in love” or not being “in love,” I’m convinced, has nothing to do with it. As long as you have someone to hang out with that night, you can always say, “well, at least I’m not alone.” And not being alone on Valentine’s Day is 99% of the battle. It’s all just about having plans and knowing that someone else, other than your parents, is acknowledging your existence on that day.

That’s why the single worst thing about Valentine’s Day is Office Mail Guy. You know him. This is the guy with the flower-filled cart that walks around your office delivering bouquet after bouquet of roses to what seems like every girl in office…except you. He’s like some fiendish messenger from Hell, determined to make you feel even more miserable about your current single, lonely status than you ever thought possible. God I hate him. Almost as much as I hate Ugly Skank Whore (who’s normally called Jenny, a very sweet co-worker of mine from Syosset, but on Valentine’s Day she becomes “Ugly Skank Whore,” my archenemy) whose cube every Valentine’s Day turns into an Amazonian greenhouse from all the flowers her boyfriend of like 10 years has sent her…again. And like annual clockwork, Ugly Skank Whore asks me to come by to “see them.” And so you have to drag yourself to the cubes of these beaming girls and tell them how pretty these flowers are, and how wonderful they smell, and coo when they read you the dinky little card…as you both sit there silently marinating in a bile of gloating and jealousy.

God I fucking hate Valentine’s Day.

In reality, it’s your own fault - you should have been planning for Valentine’s Day a month ago. With just a little pre-planning, you could have found a boy simply to make sure you had a date for the dreadful 2/14. What can I say - lack of foresight results in lack of foreskin.

But do yourself a favor – don’t go out. Stay in. You can’t take the risk of letting any of your accursed relationship friends see you on the way to a bar wearing one of your “get some” outfits. And worse, the guys that are out on Valentine’s Day are what we in the industry technically refer to as the “The Pathetic Undesirables” - the too-small fish some other girl threw back, all corralled together for one night in one desperation-tainted pond.

Just hole yourself up with two bottles of wine, run a bath, get completely Bid-Night drunk, and stew in your own lonely bitterness.

Really, it’s the only noble thing for a girl to do.


February 5, 2002

Dear Sheila,

This guy that likes me is perfect on paper, but just not cute, and I just canít get over it.Heís rich, heís smart, heís trying really hard, and it makes me feel good to have him around.And itís always an ego boost to have someone chasing after you, so I donít want to get rid of him all together, but I know that I could never date him.Is it bad to keep leading him on, just because its fun to have someone wine and dine you?And how long can I go before I have to kiss him or cut him loose?

Plastic, Not Paper


Dear PNP,

You have to use the Kiss Rule:If you can sit in your room and imagine yourself kissing this guy, then itís OK, because he still has a shot.If the thought of kissing him is unappealing, then itís probably not a good idea.And if the idea of giving him sloppy wet head makes you gag (well, more than usual) then you really shouldnít do it.But if youíre really addicted to the attention and meals, then by all means, keep him. Just keep in mind, as long as todayís best universities keeps churning out rich, unattractive future I-bankers, there will always be another night at Balthazar.




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