Miss Information

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Want to meet Miss Information? She’ll appear at Galapagos Art Space in Brooklyn as part of a dating show on Wednesday, April 12. Visit for details. Have a question? Email Letters may be edited for length, content and clarity.

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


Dear Miss Information,
    Lately I’ve been hanging out with my friend, her cute roommate and his best friend. Cute Roommate’s best friend has been hinting that he’d really like to go out with me. I’m not interested in him, but I’d really like to pursue something with Cute Roommate. He’s shy and I know I’d have to make the first move. Does this situation have disaster written all over it? I’m not sure if asking my friend to be the go-between is the greatest idea. — Eyeing Another’s Roomie


Dear Eyeing,
    You’ve got good instincts on that one. You don’t want to put your friend in a volatile situation by positioning yourself as the Helen of Troy to her roommate and his best friend. Having to share a bathroom with two guys is hardship enough.
    You may still be able to go out with Cute Roommate without offending Best Friend. Just because Best Friend likes you doesn’t mean he gets dibs. Dating isn’t about who gets there first — the affection has to be reciprocal.
    That said, best-friend loyalty is a very real thing. Sayings like “bros before hos” and “chicks before dicks” exist for a reason, so I wouldn’t be surprised if you ask him out and receive a big fat “No.” Then again, that so-called standard is not universal, and life’s too short not to ask out a cute guy who you really like.
    The next few times y’all hang out, minimize any flirting (or anything that can be remotely interpreted as such) with Best Friend. Do the opposite with Cute Roommate. Then wait and see if it has any effect. If not, ask him out more directly. I wouldn’t make it a big date — just something low-key that borders on innocent friends. Also, warn your girl. If she’s the type who blabs, tell her immediately after that fact. Finally, if Cute Roomie declines, be prepared to feel like a douche every time you visit your friend’s house.

Dear Miss Information,
    For the past few months I’ve been dreaming about my ex. These dreams always leave me feeling horrible in the morning. My friends say I should contact her to work out any unresolved issues, but I’m not interested in that. I’ve moved on to successful relationships with other girls. How can I make the dreams stop? — In Need of Quality Sleep

Dear In Need of Quality Sleep,
    Start with the usual. Establish a regular sleep schedule, take a look at any dream-inducing medications you may be taking and lay off the seven-layer burritos before bed.
    Next, try to figure out what might be causing these dreams. Keep a pen and paper by your bed and write everything down as soon as you wake up: what the dream was about and what your habits were the evening before. I know it’s a drag, but it’s important. At the very least, write about it later that day.
    You can also try something called “controlled dreaming,” which is basically making an active decision to direct the content of your dreams. It borders on the realm of what my crusty old grandma would call “mumbo jumbo,” but a lot of people find it helpful. There are tons of books on the subject, so hit up the self-help section and do some heavy-duty browsing before you buy.
    The last option is to ease up with all this self-inflicted pressure. Sometimes dreams are just dreams, and unless they involve Freddy Krueger, they can’t hurt you. It’s just your mind dealing with unresolved issues, and some unresolved issues aren’t meant to be resolved. It’s what makes you a complex and interesting person.
    Whatever route you take, you don’t have to involve your ex. Try it solo for a few months and then reconsider if the dreams persist.

Dear Miss Information,
    I met an awesome guy who happens to be a virgin. We’ve gone out a few times but haven’t had sex. I’m pretty experienced sexually, but it’s been ages since I slept with anyone like that. How can I make things go as smoothly as possible? I want it to be memorable, not awkward. — Cherry Valance

Dear Cherry,
    Picture it: West Michigan, 1993. A young Miss Information sets out to pop the cherry of her high-school boyfriend. A date is picked, parents are out of town and a fancy meal is prepared. Everything is perfect — except the sex. Drunk on cheap wine and muscle relaxants stolen from his mother’s medicine cabinet, my boyfriend couldn’t get it up to save his life. We both wound up mortified and disappointed. Later that week, we did the deed on my bedroom floor as my parents argued about taxes upstairs.
    Why am I boring you with this touching vignette? Because it’s an important lesson about first-time sex, and that lesson is: It’s probably going to suck. Don’t go all stage mom by trying to relive your first time vicariously through another person. It won’t work.
    A few thoughts for when the time comes:
    1) Plan for the act instead of planning the act itself. Have all your supplies ready (protection, lube and so on), and a rough idea of the setting, but don’t plan the exact day.
    2) Make sure you do a lot of screwing around in the weeks before. Don’t go from necking to fucking. Heavy petting, handjobs and oral sex should all be part of the equation.
    3) Most female first-timers worry about pain, but with guys it’s stamina. He might want to masturbate to climax first, or you can do it for him.
    4) As tempting as it is, don’t make it all about the “big moment” of penetration. Focus on the act as a whole. Otherwise he’s going to get psyched out.
    5) Be extra-attentive to his physical and emotional cues. If he seems like he’s not enjoying himself, let him know that the activity can stop and resume at another time. It’s not like when that big metal harness clangs down over your shoulders on the roller coaster.
Readers: Got a great first-time story? Let’s hear it. Share your experiences and stories in Feedback.

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