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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 met this guy on vacation, and we ended up having sex. Since then, we’ve seen each other and had sex several times, even though we live nowhere near each other. He continues to text me and seems interested, but after a few weeks he’ll stop responding. I can’t tell if he’s too shy to pursue something or if he’s actually not interested.
—Kay, West Village
You guys live far apart, and I assume that’s not going to change anytime soon. So, before you broach the subject, have you figured out what you want from this situation? Do you feel like you’ve really gotten to know him outside of fling-focused weekends? And are you ready to invest time and energy into a long-distance relationship? If you are, have an honest conversation with him about whether you’re both ready to explore where this relationship could go. Just be realistic and avoid setting yourself up for
I met a great guy though mutual friends, and we’ve hung out quite a bit over the past month. He came back to my place a few times but didn’t want to have sex. The first time I asked about it, he said it’s because he likes me and doesn’t want this to just be physical, but we do everything besides sex. Should I bring this conversation up again or just wait it out (though I’m getting frustrated)?
It’s only been four weeks, so I’d be more patient. It may be confusing that you two have touched most of the bases, but still haven’t gone for the home run, but he was clear and you shouldn’t pressure him. If another month passes and he still avoids sex, have a conversation about what he’s looking for and if there’s another reason that he’s not going all the way. Your chat may not result in immediate boning, but it will help you to better understand where he’s coming from (and to avoid screaming, “Why won’t you fuck me?!” out of frustration).
I’m a 36-year-old single woman looking for a relationship. I’ve been burned in the past, so I prefer to explore all other areas of compatibility before moving on to sex. How do I convey this to my prospects without scaring them off or appearing overly conservative?
—Anne, Upper West Side
Tell dates exactly what you just told me! That way you’re being clear about your intent, and you’ll know quickly whether your dates are on board with your terms or not—and if they’re not, they’re not for you. Reinforce your dating strategy by planning exciting day-dates, or ones that don’t revolve solely around drinking. Try to find experiences neither of you have had, then check them out together! Bonding over something like your first monster truck show is guaranteed to be more fun than having the same first date small talk once again.