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Let Us Sex-plain: I don’t know how many people I’ve slept with

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

By Jillian Anthony

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 can’t remember how many people I’ve slept with. Is this bad? Should I know my number?

Amy, Soho

No. Good for you for not taking up any precious space in your brain for this trivial number. I encourage each and every one of you out there to stop focusing on meaningless things like who would judge you if they knew how many people you’ve slept with (whether the number be low or high) and instead focus on having an enjoyable and fulfilling sex life, whatever that may mean for you! Celebrate freedom from societal expectations, Amy.

My ex-boyfriend promised we would get back together when he came back from the West Coast. He is back in New York, and I’m still waiting. He texts me, calls me and says he loves me and wants to be with me, but that’s when he’s drunk. When he’s sober, he ignores me. We are still having sex, and he says I am the only one, but I’ve been told he had sex with other girls. Should I let him go?

Iris, Bushwick

Iris, I’ve been there. This person is not your boyfriend, nor will he ever be. This is harsh but you need to know: You are simply a convenience to him, and he will keep treating you as such as long as you let him. If he only contacts you when he’s under the influence, it means he views you as some form of alternate reality, only someone to speak to after dusk, in secret, behind a cloak of whiskey. Break it off—right now— block his number (because he will continue to tell you he wants to be with you), and move on. You’ll find a situation much more satisfying than slurred phone calls and empty promises.

I’ve always had trouble dating, but it’s gotten worse since I moved back in with my parents after grad school. Whenever I meet someone I like, I wind up backing off because I don’t know how to reveal my living situation. Is it as much of a deal breaker as I think it is?

John, Queens

Given that you’ve finished grad school, I’ll assume you’re at least 24 years old, or maybe much older. I do think that the older people are, the bigger the likelihood they’ve moved out of the family house and expect their peers have done the same, especially in New York City, where there are so many transplants (oh, and people living off their parents’ money). But you’re making the right choice for you financially, and though it may not feel like it, that is more important than getting laid. But don’t assume people will be turned off by your familial roomies! After you’ve gotten to know someone a bit, be up front about the situation. Some people won’t care and will proceed to take you back to their place! The people who do care aren’t for you.

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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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