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Let Us Sex-plain: My crush has a girlfriend, but I know we’d be perfect together!

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

By Jillian Anthony
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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 Senior Things to Do 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!

Lately I’ve been going on dates with three guys in one night and maybe sleeping with two of them. This has been my life for a couple of months now: sex, sex and more sex. Is this bad or slutty? Or am I just being young and fun, like I keep telling myself?
John, East Village

I’m jealous, John. Make sure you schedule some time to sleep and eat, too! The only reasons your sex spree might be “bad” are if you aren’t actually enjoying yourself along the way—i.e., you’re sleeping around for self-destruction rather than self-fulfillment—or if you aren’t being safe as well as honest (within reason) with your partners. Otherwise, you sound like you’re young, fun and fabulous. Sluttiness, much like beauty, is in the eye of the beholder, so don’t even worry about what other people might think; follow your heart (or your penis) where you may.

I was married for 15 years, then divorced. The new woman in my life was married for 10 years before her divorce, after which she started sleeping with several guys, one right after another. This was right before me; should I be worried?
Steve, Sunset Park, Brooklyn

Those guys have nothing to do with you two. Shield your heart in the beginning of a relationship, and take the time to really get to know this person and the space they want to hold in your life. But if you feel great about how things are going and want to keep moving forward, don’t hold her previous sex life against her.

How do I deal with having a crush on a friend who is in a serious relationship? He ignores the texts and snaps I send him during the weekend when he’s with his girlfriend. I hate hearing him say how much he loves her and that they’re moving in together when I know we’d be perfect together!
Kate, Midtown East

Kate: Back. Off. It’s quite clear you are not this man’s friend; if you were, you might be upset about not being his first choice, but you’d be happy that he found someone to love. The fact that he ignores your messages means he doesn’t consider you a friend, either. I understand how awful unrequited love can feel, so rather than continuing to focus on what you can’t have, you should refocus on what you do have. First, minimize your contact with him, or better yet, cut off communication with him completely so you have a chance to move on. Ask yourself: If you didn’t initiate conversations with him, would you guys talk at all? Try to think objectively about what value this person adds to your life (I’m guessing it’s little). And start doing way more of the things you love, whether that’s a yoga class or karaoke or writing that novel you’ve been putting off.

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Read previous weeks’ sex columns

let us sex-plain
Photograph: Shutterstock

Let us sex-plain

Sex and dating

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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