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Let Us Sex-plain: Is it possible to truly just be friends with benefits?

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

Illustration: Alex Citrin

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!

I’m not looking to just get laid on dating apps, but it seems that most girls I talk to on them are. How do I make it clear that that’s not what I’m looking for?
—Byron, East Village

Be up-front and put something on your profile that’s clear but not overly aggressive, like, “Looking for a relationship” or “More into sixth dates than first dates.” Online dating, or any kind of dating, is tricky because you can never be sure of someone else’s intentions, but here’s how to protect yourself: Go slowly, make your intentions known, and get to know someone before you sleep with them. You can only control your own actions in this life, so you do you, and you’ll find the right person along the way.

Because I was really skinny in my early twenties, I’ve been boxed in as a twink, and I’m ready to grow out of it. But how do I reteach myself—and prospective mates—that I’m a mature sexual being and not some toy for older men?
—David, Crown Heights

Several of my gay friends have experienced the kind of labeling (otter, daddy, etc.) that you have. I asked them about your dilemma, and they offered three pieces of advice: Reevaluate your appearance, get out of your comfort zone, or stop giving a fuck. “As much as we all say, ‘We are a gay family, kumbaya my Lord,’ I’ve yet to meet anyone who doesn’t judge anyone else,” says Mikey (yes, all humans judge the hell out of each other). So, if it will make you more confident, change up your look and hit the gym. Alternately, take a close look at your dating habits. “Maybe you put off twink vibes because that’s where you’re comfortable,” says Shain. “It’s like when people only bottom because they’ve never topped—it’s what they know.” Try dating those you normally wouldn’t, and switch up your dating apps or where you hang out. Finally, you can make a choice to own who you are and accept your body type. (This one gets my vote!) Don’t grow out of it; grow into it. “Being emotionally mature is not about who you bang,” says Danny. Amen.

Is it possible to truly just be friends with benefits? How can I achieve this?
—Asha, Flatiron

Yes, it’s possible, but it’s certainly not common. Sex creates oxytocin, a chemical that promotes bonding in our brains. (Science!) If you really want to be fuck buddies with someone, set boundaries with yourself and the other person. Maybe you don’t see each other more than once a week, or you have a don’t-ask-don’t-tell policy about other partners. Of course, your libido might get in the way of your rules, especially when combined with our pal booze. But most of all, respect your own needs as well as your partner’s, and if the sex stops feeling good emotionally, even if it’s still good physically, move on.

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Read previous weeks' sex columns

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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By: Jillian Anthony