Miss Information

Pin it


Have a question? Email Letters may be edited for length, content and clarity.

Dear Miss Information,

I'm crushing hard on this incredible woman. She's talented, funny, smart and beautiful. Some time ago, I went on a few dates with a friend of hers. Nothing came of it, and I haven't met up with the friend since, nor do I intend to ever again. In your understanding of girl etiquette, what's the best way to handle my attraction to Amazing Woman? And furthermore, if I do ask her out and she begs off "because of her friend", isn't that just a nice way of saying she's really not interested?



Dear Neurotic Guy,

Speaking as someone in possession of a pair of tits, I can tell you that "girl etiquette" is as varied as ladies themselves. Some of us will throw over our best friends for a piece of late-night tail, even if he looks like Meat Loaf by light of day. Others hold the girl code so high that a mere glance at a guy a friend crushed on a decade ago is grounds for a permanent write-off.

Without knowing what your "few dates" with Amazing Woman's friend entailed, it's safe to say your chances are better if you didn't do the deed. If you and her friend did fuck, you'd better be able to say things ended very amicably. Otherwise, you're wasting valuable time I could spend watching reruns, forearm deep in a bag of Cheez Curls.

Assuming everything's fine on the friend end, it's up to you to win over Ms. Amazing. Do that by making it perfectly clear you no longer have any interest in her friend. That means no flirting, no talk of past dates and no compliments on the friend's new dress/job/throat piercing. Finally, see if you can enlist the help of your former flame — a few good words from her can go a long way.

If you do all this and she still doesn't bite, she could be "not that kind of girl." Or she is, but not with you. Even if Ms. Amazing is Ms. Thinks You Suck, sometimes little white lies are better than ugly-ass truths. So try to take it gracefully and move on.

Hi Miss Info,

I was engaged to this girl I'd been with since high school, and nine months ago she broke it off. Over the ensuing months, we kept on sleeping together. She hinted that she wanted to get back together, that she wasn't sleeping with anyone else and that I shouldn't either.

A few weeks ago I discovered that she had, in fact, slept with half of Toronto and is pregnant!

After my initial rage, I decided the smartest thing to do was go out drinking and screw the first girl who showed an interest in me. Unfortunately, it was my best friend's housemate. I thought it was obviously just a drunken one-night stand. However, during a sober encounter a few nights later, she post-coitally murmured, "I have a problem — I really like you."

I tried to tell her that I wasn't able to do the relationship thing. She says she understands and is happy keeping it totally casual. Now every time I visit my friend she greets me at the door with a kiss and assumes I'll be staying the night.

I don't want to hurt her, and I don't want to make things awkward for my friend. I really like sleeping with her, but I'm still fairly screwed up about my ex, and the last thing I want is a relationship.

Confused Canadian

Dear Confused,

You're slower than maple syrup if you thought sticking your dick in this girl wouldn't encourage her to form some sort of attachment. Granted, she committed a major fuck foul by saying she was okay with keeping things casual, then acting otherwise. But now it's up to you to end the game.

A douchebag rookie will continue to randomly sleep with her, acting alternately friendly and distant, until he finds somebody better and acts all surprised when Ms. Fuck Friend is hurt. A pro will take a two-pronged approach, telling this girl that there's no possibility of a relationship and then putting his dick where his mouth is (not literally — though send me some photos if you want to try) by NOT sleeping with her.

Obviously, this is easier said than done. But consistency is key. In a perfect world, you two would be able to bone away with incident. But because she likes you more than you like her, it's your responsibility to exhibit greater willpower. Turning down casual sex (especially good casual sex) feels about as fun as filling out a stack of 401k forms, but take comfort in the knowledge that you'll have better dating karma than your no-good ex. And at least you're not cleaning up baby shit.

Dear Miss Information,

I'm trying to figure out the classiest oral sex "finishing" etiquette when dealing with a guy. I feel as though my only options are (a) Freak out like a nervous high-school girl and make him wiz on himself, then clean himself off, or (b) Make like a porn star and pretend I love it in my mouth and all over my face, where it inevitably ends up. I am a sophisticated and smart woman. How should a sophisticated and smart woman deal with wiz?

Yes. I used the word "wiz."

Signed, The WIZard

Dear WIZ,

Gee whiz, WIZ. Sounds like you've got a wicked case of the madonna-whore syndrome. What else can explain a smart, sophisticated woman attaching complex personas to a physical act that's as simple as spitting vs. swallowing (high school girl and porn star, respectively).
Forget how you look to your guy — what's classiest is what makes you most comfortable. If you act like you're fine getting a faceful, then run to the bathroom to throw up twenty seconds later, chances are you're not going to come off like the worldly dame you want to be.

However, if you decide to do the big finish, preparation is key. Spitters are going to want somewhere to put their man-present, be it a Kleenex, a towel or a spare T-shirt. For those who do the Big Gulp, a glass of soda/coffee/bong water on the nightstand definitely comes in handy. Sure, everyone looks a little stupid when they're spitting jizz (excuse me — wiz) into a sweat sock or gargling with day-old Pepsi, but like it or not, that's sex in all its goofy splendor. Soft lighting and perfectly mussed hair only happen in Meg Ryan movies. And I can guarantee she doesn't go down half as well as you do.

One buzzkill: a variety of STDs can be transmitted during unprotected oral sex. So if you're not sure your partner is clean, your health is the perfect excuse to use a condom during oral and forgo the facial fireworks altogether.  

Previous Miss Info

©2005 Erin Bradley and