Let Us Sex-plain: Why can I only have good sex with strangers?

Your personal wingwoman, Jillian Anthony, answers all your questions about dating and doing it in New York
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Illustration: Marina Esmeralda
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I get it—being single in the city can be tough, and the ways New Yorkers are having sex these days can be surprising. But whatever your dating conundrum might be, I'm here to help. Consider me (Jillian Anthony, Time Out New York's Editor) your personal wingwoman, guiding you through dating and doing it in New York in our weekly "Let Us Sex-plain" column. Check out my answers to all your questions online and in the magazine every Wednesday, and submit your own coitus queries below!

I feel like I’m having the best sex of my life but only with strangers. Every time I’m into someone, the sex just isn’t as good. Halp.

—Tom, Bed-Stuy

There’s nothing wrong with great sex with strangers! But if great sex seems to only extend to people with whom you’re not emotionally intimate, that’s an issue. You can sit with yourself and try to identify how having sex with someone you care for makes you feel (anxious? vulnerable? no longer in control of the situation?) and confront those feelings to find their root—like a past breakup that’s still messing with you internally. But if you have the means, I’d advise you to go to a psychologist to work these things out before they take more of a negative toll on your relationships.

My friend set me up on a horrible blind date. I’m really tall, and she was really short, plus she was unattractive and possibly the most simple person I’ve encountered. What do I say back to this friend? Is this what they think of me?

—Adam, Williamsburg

Unless your friend is actually your frenemy and mismatched your date on purpose, there’s no reason to chastise them. Perhaps your friend knows this woman in a different light than you do or never considered the disparity in height. (Side note: Height, much like skin or hair color, isn’t something one can choose, so it’s about time we untrain ourselves to use height, or lack thereof, as an acceptable dating prejudice. Think of the giant pool of incredibly tall or short people you could be automatically crossing off your list!) My point is: Don’t read into it too much. Now you know this friend doesn’t quite understand your tastes, so you can be honest and say the date didn’t go well, and be more clear about what you’re looking for—or just don’t accept another setup from them in the future.

I’ve been dating my boyfriend for over a year now (including some nonexclusive time), and recently our sex life has become so vanilla. We spoke about it, but it only picked up briefly before going back to boring. We had awesome sex before, but it’s been different since we committed to a relationship. What should I do?

—Jane, Crown Heights

This dip in your sex life could have nothing to do with your recent commitment. It could be a natural decline in the passion and urgency of early-relationship sex, or it could have to do with something your boyfriend is going through that has nothing to do with you. Whatever the cause, it’s great that you guys are already talking about it. Keep communicating how important this is to you, and remember to also take on some responsibility for introducing spontaneity and new tricks into your sex life. See how things go over the next few months, but don’t give up yet!

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Sex and dating

Let us sex-plain

Your personal wingwoman, Jillian Anthony, answers all your questions about dating and doing it in New York. Read them all here.

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