Miss Information

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

Dear Miss Information,
My boyfriend loves to go down on me. I’m kind of "whatever" about it, because I rarely come that way. I have a hard time relaxing and tend to get stressed about it (do I smell? etc.). The last time he gave me oral, I started fantasizing and ended up coming. I know that sometimes you just have to fantasize to get the job done, but I’ve become paranoid that if I don’t do it, then I won’t come. My boyfriend would die if he knew, and I’m afraid it’ll one day slip out that I’m dreaming about a hot blonde between my legs instead of him. But if I don’t fantasize, I’m worried I’ll disappoint him by not coming. — Should I or Shouldn’t I?


Dear Should I or Shouldn’t I,
Exactly who is this hot blonde? If it’s someone like Beck or Maria Sharapova, then who the hell cares? Your fantasies are your business. Unless you’re having daily, detailed scenarios of hate-fucking your ex or nailing your boyfriend’s best friend, stop taking it so seriously. Getting head is supposed to be fun, not a luxury cruise aboard the Guilt Ship Lollipop.
    Sorry to break it to you, but chances are your boyfriend has thought about someone or something else while you two were having sex. That might make you feel a little skeeved out or sad, but his dirty daydreams (just like yours) don’t signify that he loves you any less. If you still think it’s a big deal, try only doing it every other time or just cut it out altogether. As you do so, get your guy used to the idea that you might not always close the deal. I get the feeling there’s a lot of pressure for you to perform – this “disappointment” shit is a little much. It’s sex, not an athletic competition or a Junior Miss Alabama pageant.
    Finally, get your guy involved in your smutty flights of fancy. He doesn’t have to answer to your cries of "Fuck me, Mr. Depp!" but he could help you recreate the places (backseat of a car, bathroom of a club) and scenarios (he’s the student, you’re the tutor, etc.) that help get you off. Fantasies are about much more than the people in them. Good luck.

Dear Miss Information,
I’ve been dating since I was fourteen. I am now twenty-five and will be going it alone for the very first time. After living with my partner for the past eight months, I’ve decided to move back home to start a new life. What prompted this decision was my realization that I no longer want to be dependent on men . . . for anything. I want to prove to myself that I can make it on my own. On one hand, I’m excited and anxious to take a chance on life again, get closer to my mother and to meet to new people. But on the other hand, I feel guilty because I will be leaving my partner behind. He says that he wants me to be happy, but I know he does not want me to leave. I know in my heart I have to do what’s right, even if it means possibly losing him. Despite the move, we have decided to date long-distance and to see each other when we can. My questions are this: How do I start my new life on an even keel and not feel guilty about this decision? And should I break things off with my partner or not? — Happily Alone Again (Almost)

Dear Happily Alone,
At the risk of sounding like a Werther’s Original commercial, your letter reminds me of myself at your age. In the midst of a quarterlife crisis, I decided that leaving my boyfriend of three years and moving to New York City was the only way I was going to find out "who I was." Three years later, that person would emerge as someone who writes dirty for a living and spends an exorbitant amount on sushi and disposable umbrellas.
    I don’t regret my move for a single second, but I do regret the way I fucked things up with my former beau. For the last year and a half of the relationship, I’d been pulling away emotionally (mood swings, distant behavior) and physically (packing my shit into the back of a U-Haul). I told myself I was doing this because I needed time to grow and be on my own.
    But the other half of the story, the part I really didn’t want to admit, was that I was just not in love with him. I mean, I did love him, but it wasn’t the kind of love in which I wanted to be with him forever and ever Barbie-Dream-House-style amen. So I used him as my emotional safety net until I got the guts to strike out on my own, screwing with his self-esteem and ruining our chances of ever having a workable friendship.
    What can you learn from this little morality play? It’s important to do what you want, when you want to do it, and you don’t need this guy (or anyone else) for a security blanket as you live out out your rock ‘n’ roll fantasies. I’m not saying you should dump him, but think seriously about what you want from this relationship before putting him through the stress of long-distance dating. If it’s just postponing the inevitable, then let this guy go.

Dear Miss Information:
I am a married man in his forties with two children. In ten years of marriage, I’ve never had an affair. Last weekend, a group of old school buddies met up at a local bar for cocktails. One woman in particular — let’s call her “Sandy” — was very friendly with me. We had a great conversation about old times, our lives and our current circumstances. She is also in a committed relationship with a man she says she loves deeply. I’ve always felt an attraction to her and have sensed she feels the same, but given the circumstances I’ve never acted on it. Leaving the bar, Sandy (who was very tipsy, to say the least) began rubbing my neck and shoulders. Before the group went their separate ways she gave me a warm hug.
    Earlier in the evening I had told her that I was a private pilot and, without any conscious ulterior motives, offered to take her flying. My two questions are: With her guard down because of the alcohol, was Sandy sending any signals that I should be aware of? And two: Do you think I’m putting myself in a potentially dangerous (sexually) situation by spending time with her (or with her in this particular group in bars for that matter)? — Wants to Do the Right Thing

Dear Do the Right Thing,
You’ve known Sandy a hell of a lot longer than I have, so only you can tell whether she was putting the moves on you or just being a flirt. My experience has been that if you sense an attraction (and you don’t look like Jon Lovitz), there’s probably something there. Intuition doesn’t lie. Not that you’d need it — the "friendly neck rub" is right up there with Tom Jones records and satin sheets as one of the cheesiest seduction techniques of all time.
    Good news and bad news for you, Do the Right Thing. The good news is that you don’t have to cancel your next boozy class reunion. This is the first time anything of this nature has happened, and there is a chance (however slight) that Sandy was just being a horndog because she was super-drunk, ovulating, or both. Try to get a better gauge the next time you’re out. If she still seems like a flirtbag, invite your wife to your next get-together, or at least let her know what’s going on. There’s nothing like an informed spouse to rein in an errant boner.
    The bad news is that you have to cancel your private plane ride. Maybe you’ve been a pilot a long time and you’re a little jaded, or maybe you’re in denial, but here’s a quick announcement from the flight deck: Flying is hot. People who fly for a living are even hotter. Inviting Miss Sandy to see you do what you do is the equivalent of Ron Jeremy inviting your wife to come see him on set. Unless you secretly want Sandy to wind up sucking you off, don’t make these kind of offers. They don’t call it a cockpit for nothing.  

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