Miss Information

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

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.

Dear Miss Information,
I love to go down on my girlfriend. But the last time I gave her oral, I was bothered by the fact that she doesn’t shave. It’s never been a problem for me in the past, but now the only thing I think about when giving her oral is how great it would be if she were significantly trimmed down. Personally, I take care of myself, and make sure that I’m not out of control down there.
    In the past, she told me that she doesn’t know why someone would shave their entire genital area. How do I kindly ask her to shave without looking like a complete asshole? — Likes It Bare

Dear Likes It Bare,
You’re right to approach this one with caution. Even though a lot of people (including you) file it under the category of "taking care of yourself,” shaving your pubic hair is not the same as slapping on some deodorant or putting on a fresh pair of BVDs. If it were, we wouldn’t be having this discussion.
    Here’s what you want to do: make it more of a sexy suggestion rather than a reminder that something’s been neglected. After all, she might not view it as neglect if she doesn’t think she needs to do it in the first place, and you’ve never bitched about it before.
    Start by telling her how much you love spending quality time between her thighs and how hot it would be if you could get a little closer to the goods. Asking her to go completely hair-free might be a little much right out the gate, so suggest a trim and see how she reacts. Alternately, you could buy her a pair of ultra-skimpy underpants and suggest a new pube ‘do to go along with them.
    As a middle-of-the-roader (i.e., clean and tidy but not bare) who has received requests to shave from more than one beau (and has occasionally obliged), I can tell you what’s not going to work: glowing references to pube-free porn stars or ex-girlfriends, whining about getting hair in your mouth (try deep-throating a large foreign object and then get back to me), and mentions of your own perfectly groomed Johnson.
    She might go for it, she might not. Ultimately, it’s her crotch and her decision, so try to be cool about it either way.

Dear Miss Information,
I recently went on my third date with a guy from work. We both had a great time — he even called me after I got home to tell me so. He said I should call him with details for a tentative date later that same week and also suggested we go to a show that Sunday. I called, as he requested, but he hasn’t returned my calls. It’s been two weeks. Is he not interested? Is it worth trying to figure out what’s up? — Weak After Two Weeks

Dear Weak,
Chances are this guy doesn’t dig you. Two weeks is a long time, and unless there’s a candlelight vigil being held outside his cubicle, I’d say "fuck it" and move on.
    I know you two got along well on your last date, but that’s not always a guarantee. People behave in unpredictable ways and we daters get to bear the brunt of it. The upside is that we can ditch someone when they start being a pain in the ass without involving a notary public.
    If you’re hell-bent on prolonging the agony (and who isn’t?), you’re entitled to one more call or email in which you say something like this: "Dear Boy, Hi. Haven’t heard from you in a while. I’m guessing it’s because you’re not interested in going out again. Or maybe you’ve been busy and haven’t had the time to respond to my messages. I’d appreciate a quick note to let me know what’s going on, and no hard feelings either way.”
    You can modify it to suit your needs, but the point is to keep it civil and brief while making it clear that you’re soliciting a yes-or-no response. If he doesn’t answer, know that you’ve taken the high road and saved yourself from continued couplings with an immature coward. If, by some miracle, he comes back at you with a good excuse, put him on probation for a few weeks. Make him do all the work — calling, date planning, you name it. Disappearing acts belong in Vegas with that asshat David Blaine. Don’t put up with a repeat performance.  

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