November 13, 2003
You hate me.
Seriously, I'm working on getting on track. If you sign-up
for the comic, subscribers get updated when a new Sheila's Male Bag is
Got your own question for Sheila? Send it to firstname.lastname@example.org.
October 30, 2003
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
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.
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!”
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
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
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.
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
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
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
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
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
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
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
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
There are two types of girls in the world: those that believe oral sex
always comes before regular sex, and those
Personally, I am a strict adherent to the traditional hook-up orifice
sequence: manual (kind of an orifice), oral, vaginal, and lastly, on special
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
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
September 27, 2003
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
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
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
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
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
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
- 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
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.
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 www.sexuality.org 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
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
How does your boyfriend feel about hummus?
August 28, 2003
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?
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
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
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
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?
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
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
Pimple Popping Pleasure
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.
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
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
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
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
Hello?Notreallyfriendsaphobia - Fear of getting asked
to be a bridesmaid of someone you know you won’t ask to be one of
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
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
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.
Staring at Ambiguity
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
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
- Are all his shirts and sweaters one size too small, and disproportionately
- 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”
- 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
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
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
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
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
Just make sure they include an apple martini (or three) this time.
June 18, 2003
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
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
…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.
…friends from college or high school you could care less if you
…like that Stephanie Blankstein bitch from 11th grade. [-5]
…who has reportedly put on 30 pounds since having her three illegitimate
3. It’s confirmed. You’ll be sitting at the singles
…not knowing anyone else there. [-15]
…but there’ll be a 4:1 ratio of single guys to single girls.
…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
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
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”
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
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
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
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
But at least you don’t have to spend your Sunday washing man-butter
out of your sheets.
May 28, 2003
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
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
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
After that, I promise he’ll think your little gas issue is cute
as a button.
May 21, 2003
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
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
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
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
And really, aren’t we all just looking for a date that isn’t
a waste of a good thong?
May 14, 2003
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
The Premature Birthday. Always an awkward moment early in a relationship,
right behind “The Premature Valentine’s Day” and “The
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 –
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
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
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
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
- 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
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
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?
BECAUSE WE FUCKING SAID IT IS.
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
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
And I dare you to take it with a smile.
April 23, 2003
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
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
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
- 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
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
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
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
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
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
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
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
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
I’m thinking about shaving off all my pubic hair as a surprise birthday
present for my girlfriend. What do you think?
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
You give bad head.
February 12, 2003
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?
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
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
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.