Claire, 26

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What's a good technique for approaching an attractive stranger on the street?
Ask them where they got that sweatshirt/book/tattoo, and if the store where they got it is near their neighborhood, and then what their favorite spot is over there. Then post a Missed Connection.

I'm shy. How can I seem more gregarious and less withdrawn when speaking with someone I have a crush on?
I live by at least two or three cliché mottos involving regret: It's better to regret something you did than something you didn't do; do something everyday that scares you; it is better to have loved and lost . . . you get the picture. You really have nothing to lose. Realize that your crush is a normal person. It's like meeting celebrities — just be natural and don't freak out.

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Can I give a fake phone number to someone if they ask me for mine but I don't want them to have it?
Absolutely. I once read that Marilyn Monroe would give people the number to the L.A. County morgue. I don't know if it's true, but I would do that in a heartbeat.

I just moved to a new city. How can I find a date without anyone to go out to the bars with?
Never underestimate going to the bar alone. Try the bathroom line for same-sex future wingmen. And "I just moved here" is gold — people are always happy to show off their city.

My boyfriend wants to have sex every night, but I'm more of a once-a-week girl. Can we reconcile this, or are we doomed?
You have to meet in the middle, or he might start looking elsewhere for his kicks. Film yourself jilling off for him to watch when you're not in the mood. I bet you won't be able to ignore him for long.

What phrase should one never include in an online ad?
"Long walks on the beach" as a form of irony is about as annoying as that guy at the Lightning Bolt show screaming, "FREE BIRD!"

Frank, 28
www.lattelib.net

What's a good technique for approaching an attractive stranger on the street?
Anything, however lame, will work. "Hot today." And, "Are you waiting for the L train?" It doesn't matter, just something that elicits a response. From there you can gauge whether she's interested.

What phrase should one never include in their online ad?
"Love to laugh." "Love to have fun." "Want a guy with a sense of humor." Basically anything that anyone would be crazy not to want. I once composed a personal ad that consisted of all these phrases negated: "I want girl who's out of shape, unattractive and hates life." It got lots of responses from people sick of hearing the same five lines in a different order.

In what situation is it appropriate to take a phone call during sex?
An imminent terrorist attack. That is the only situation. Ever. If your partner does this otherwise, stop having sex with them and leave.

Is it ever acceptable to give someone a fake phone number?
Yes. This is a totally acceptable diss. Much, much better than getting the correct number and then having her ignore your calls or answer and be disinterested. That wastes everybody's time. If you get the fake number, you get a little ego boost when you need it, and nobody's time is wasted.

What's the best way to deal with awkward silences on a first date?
Don't try too hard to fill them. Let a couple of them stew for a while. There's something to the theory that goes, "That's when you know you've found somebody special: when you can just shut the fuck up for a minute and comfortably enjoy the silence."


Helen, 19

What's a good technique for approaching an attractive stranger on the street?
Asking for directions. Especially in New York City, it's so easy to just pretend you're a tourist and approach anyone for directions. Bonus points if you can play the flustered, lost girl/guy act and pull it off as cute.

What phrase should one never include in their online ad?
"I'm exactly the type of guy/girl that you want." It just reeks of cockiness. Why would you be writing personal ads if you fit everyone's dream-mate prototype?

My boyfriend wants to have sex every night, but I'm more of a once-a-week girl. Can we reconcile this?
Sexual compatibility is important in a relationship, but it's not the only component. You should have a talk with your boyfriend to reach a compromise. If your boyfriend refuses to listen, you should ask yourself if he's really dating you for you, or for your vagina.

What's the best way to deal with awkward silences on a first date?
Stuff your mouth with food or drink. Seriously, it works.

I just moved to a new city. How can I find a date without anyone to go out to the bars with?
Public places like parks and especially subways are excellent forums for meeting people. The main thing to remember is to take things lightly. Meeting people should be fun, not stressful.

Is it ever appropriate to take a phone call during sex? If so, in what situation?
I'll say no, but I'm a hypocrite. Justifiably, the only times I've done so are when my parents call and they think I'm in my dorm doing homework while in reality, I'm riding a guy on his sofa.

Where should I try having sex that I've probably never tried?
Break into a classroom. The whole "we could get caught by a janitor" mindset makes the act so much hotter.


Justin, 28
www.myspace.com/ankreefrent

I found out that my girlfriend has been telling her friends all about our sex life. This bothers me and I asked her to stop. She thinks I'm being a prude. Am I?
The same way there are things that are easier to discuss with your closest guy friend than with her, she may have a need to talk with her friends. If you think she's just being a gossip or co-ruminating, tell her you'd really like her to respect your feelings. If you're maybe (just maybe) being a little too uptight and could give her a little slack, why not?

What's a good technique for approaching an attractive stranger on the street?
Honestly, from four sisters, a slew of women friends and my own occasional success, women like confidence. The shy, bashful thing wore off in middle school. Be assertive but not arrogant, and be yourself. If self-deprecation is your thing, be sparing with it — that should be eased into.

I just moved to a new city. How can I find a date without anyone to go out to the bars with?
Back when I moved to Baltimore, I got lucky. I was sitting alone in the back of a packed bar/lounge on a three-seater with a little table, and my now-ex-girlfriend-but-then-stranger walked up and asked if I'd share my real estate with her. Aside from dumb luck, try parks, community events, volunteering, coworkers, coffee shops, etc. Also, try having a great ass. If all else fails, find something you really suck at, make a big clumsy scene sucking at it, and hope for some "awww" points.

Is it acceptable to give someone a fake phone number?
Sure it is. My cell phone is chock-full of them. I mean it is not. Honestly, it's not the worst offense ever. Some people feel bad having to reject someone, and some people would rather not be rejected face-to-face. When you put someone on the spot for their personal info, it's their turf, and they get to decide how they want to let you down.

In what situations is it appropriate to take a phone call during sex?
If your mother or father is calling at three a.m. and that's uncharacteristic, it's probably reasonable to pause and see what the emergency is. Same as if you get a collect call from the county prison — unless that's your other lady.

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Interviews by Kate Worteck. Sex Advice From... appears on Thursdays. Have questions for the general public? Send them to .