Miss Information

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A Message from Miss Information: I’m heading home this week, where I’ll be eating marshmallow-topped sweet potatoes, fielding invasive questions from relatives and watching the Detroit Lions lose. An all-new Miss Information will return next week. Til then, enjoy this Thanksgiving “Best Of” and remember to write me at should any of your holiday entanglements go awry.

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


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,
    How do I get my new boyfriend interested in performing oral sex on me? We have sex regularly and I’ve performed oral for him. When I bring it up, he says that he likes doing it sometimes, but doesn’t want to be pressured into it. We’ve been going out for a month and he’s only gone down there once to examine the area and suck on my clitoris for less than thirty seconds. I don’t want to pressure him. He’s a very supportive boyfriend and I feel like I’m in love with him. What should I do?
Feeling Licked

Dear Feeling Licked,
    In high school, whenever I wanted to avoid doing stuff I didn’t want to do (pretty much everything except sulking and listening to shitty goth music), I would tell my mom that I was more than willing to do it, if only she would stop pressuring me. In reality, I was just a normal, surly teenager, and taking out the trash, calling my grandma and writing my college essays were the last things in the world I wanted to do. No amount of pressure (or non-pressure) was going to change that fact.
    What I’m saying is, the whole “lay off me” routine was just an excuse. Such is the case with your boyfriend. People seldom put off shit they genuinely want to do, particularly when it’s part of what most people consider sexually routine. It’s not like you’re asking him to sign up for hormone injections or shove a monster-sized dildo up his ass for the first time.
    It is theoretically possible your boyfriend does want to go downtown, but he’s shy and thinks he’s no good. Either that, or the last girl he ate out tasted like canned salmon from the dollar store and now he’s repulsed at the very thought. You’re not going to know which one it is until you two talk. Any guy who wants to keep getting laid is probably not going to tell you he doesn’t dig eating pussy, but at least you can get more of a feel for where he’s at on the oral issue.
    If your boyfriend refuses to give in (or at least compromise), you’re going to have to decide your course of action. You can try withholding blowjobs from him, but no one really wins in a sexual cold war. Things just escalate and lead to more crappiness, like that Scorpions song about the Berlin Wall. Remember: unless you’re both getting what you want and need, you two probably aren’t sexually compatible, and it’s best to part ways before you get any closer. Your pussy (and your sanity) will thank you.

Dear Miss Information,
    I’ve been with a married man for about two years now, and there seems to be no stopping us from doing what we’re doing. I’m happy with the intimacy, lack of real commitment, blah blah blah, but once or twice I’ve been tempted by other guys. So, in light of the circumstances, if I sleep with another person is it really considered cheating when my “boyfriend” is already married? I know it’s not the greatest situation any way you slice it, but at least let me know if I’m right or wrong. Thanks! — Two-Timing the Two-Timer

Dear Two-Timing,
     Yeah, it’s cheating. Even though he’s married, he’s operating under the assumption that he’s the only one you’re fucking. If you hook up with someone else and lie about it, either directly or through omission, you’re playing by a different set of rules. As one of my readers put it a few weeks ago, that’s the very essence of cheating, toots. You could argue that crooks and liars are bound to no moral code, hate the game not the playa, blah blah blah, and you’d probably sway me a little. But why would you want to make a complicated situation even more shitty and dramatic? Maybe you’re vying for a spot on Montel?
     Tell your married man you want to (and are going to) fuck around. End of story. What’s he going to do if he doesn’t like it? Tell his wife

Dear Miss Information,
Some time ago my fiancé’s brother’s girlfriend, Annie, came from her home country to stay with me and my man. We got along amazingly well. She’s bright, pretty and innocently sexy. After a night of hot dancing at a lesbian-friendly nightclub, I seduced Annie, who hadn’t seen her boyfriend in months and was uncontrollably horny. My fiancé didn’t mind, as long as I kept the details to myself, because Annie will likely one day be his sister-in-law. Annie’s boyfriend, Carl, was a little jealous at first, but he eventually got over it.
     Now my fiancé and I are going overseas to meet my future in-laws. Annie is impatient to show me around town. She wants to arrange some girl-on-girl encounters for me and would probably want to watch but not participate, because Carl probably wouldn’t be cool with it. I would love to have another go with her, and I suspect she’d be burning for it, too. Do you think it’s worth the drama to try to get Carl’s blessing for our little affair? — Future Sister-in-Law

Dear Sister-in-Law,
No, I don’t think it’s worth it, but promise to let me watch if you do. This letter is HOT AS HELL, and it’s making a masturbation break look like a very real possibility.
     But that’s just my vag talking. Luckily, my brain knows better, and right now it’s saying that fucking and family don’t mix. Even if it’s only at the in-law level, the risks are too high (trashed relationships, a family tree that looks like a Mobius strip) and the returns are too low (a feel-good fuck you could always get elsewhere).
     You’re better off viewing Annie as a fond memory then trying to convince her boyfriend for another go-round. If you don’t listen to me, you’d better be prepared to keep your word when you talk to Carl. Asking for someone’s blessing is just that: asking. If he says no, hands off his hoochie.

Previous Miss Info

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