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I get it—being single in the city can be tough, and the ways New Yorkers are getting it on 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 here!
How do you keep a guy interested if you sleep with him the night you meet? Is it game over?
—Yoko, Chelsea
The myth that a man won’t take a woman seriously if she sleeps with him (a.k.a. why buy the cow if the milk is free?) is sexist, outdated and deserves a swift death. If you’re sleeping with someone because you want to, that’s the right time, whether it’s the first date or the 10th. Any man who holds sex against you is someone you should run far away from—ain’t nobody got time for old wives’ tales that hold women back. If a man sleeps with you on the first date, is he a slut? Do you disrespect him for giving it up so quickly? Probably not, and anybody who perpetuates that bullshit stereotype needs a lesson in feminism and equality.
My boyfriend lasts forever when we have sex. My friends say that’s a good thing, but it feels like too long and starts to get uncomfortable. What can I do to speed things up?
—Molly M., Gowanus, Brooklyn
People may think this situation is enviable, but until you’ve experienced it, you have no idea what it’s like when your partner says, “Round three?” after having sex for two-and-a-half hours, and you find yourself screaming, “Can I at least take a break to eat a sandwich?!?” Having sex all night long, as the songs go, is more enjoyable as a treat than an everyday occurrence. Instead of trying to speed things up, I’d advise taking the pressure off mutual climax. Sex shouldn’t always be about the end—it should be about the journey. Enjoy the experience rather than making it a race to the finish
line. Alternatively, since he’s the No. 1 fan of his own penis, feel free to let him masturbate till he’s almost there, then quickly take him somewhere over the rainbow.
Where the hell do I meet people outside of bars and Tinder? Is it even possible?
—Jamie A., Williamsburg, Brooklyn
Once upon a time, in a galaxy far, far away, it was considered unacceptable for men and women to mingle in places where alcohol was served, and we were not yet plagued by a scourge of dating apps. But the two sexes still found ways to meet, date and fornicate, and you too can achieve this elusive goal! Let’s start with the scariest piece of advice: Go places alone. This leaves you free to strike up a conversation with that guy pondering your favorite Monet at MoMA and makes you more approachable. Next, become an activities person. Sign up for a kickball team, a taxidermy class or a book club—whatever you’re into. (The likelihood of meeting people IRL skyrockets if you’re putting yourself out there.) And finally, say hello. The very worst thing that cute guy on the subway could say is “I’m not interested”—and you’ll live to flirt another day.