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Illustration: Alex Citrin

Let Us Sex-plain: My boyfriend insists on telling me all about his past hookups

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 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!

Every time my hookup and I have sex, she immediately runs to the bathroom to “clean up.” It weirds me out. Is it okay for me to ask her to stick around for a second?
—Bill, Upper West Side

It’s normal to want a few minutes of cuddle time post romp. First, ask her why she’s so quick to head to the loo. She could be hyperworried about getting a UTI (always pee soon after sex, ladies, but you don’t have to sprint straight from his penis to the toilet), she could feel dirty (physically or mentally, and if it’s mentally, that could be a huge issue for your sex life together), or it could be something else altogether. Hopefully she’s open to discussing her worries, and if so, tell her how much you’d like it if you could hold her for a bit after sex.

I’ve been on six dates with a guy I really like. I thought he was just being a gentleman by not asking me to come home with him yet, but last night he told me he’s a virgin who wants to wait until marriage. I’ve been having sex for a decade! Should I see where this goes or call things off now?
—Dina, Crown Heights

This guy has every right to make his own choices, but sex is a natural and positive part of life for most adults, a part I’m assuming you highly enjoy. Six dates isn’t very much time to get to know someone, but if you truly think this guy might be your future husband, it’s up to you to decide whether abstaining from sex and all the other intimate things that come along with it (like maybe never sleeping at each other’s places and sharing a sleepy morning together) is a worthwhile and realistic sacrifice for you. If it’s not, let this guy go; you’re not on the same path.

My boyfriend is great, but he has a habit I can’t stand: He always talks about his past sexual conquests in detail. I get that he’s been with other people, but I don’t want to hear about it! He says I’m being “immature.” Who’s right?
—Becca, Lower East Side

I had an ex like this. When he brought up his cool sex stories from college, it always sounded like he was trying to impress me, and trust me, it didn’t work. I’m all for sharing information about past relationships and experiences that mattered in your life—we’ve all learned important lessons along the way—but telling me how hard you made a girl come in a concert hall bathroom one time isn’t something I need to hear, nor is it information that can help a budding relationship grow in any positive way. It’s perfectly fine for you to ask him not to share play-by-plays of sex with his past lovers; if he doesn’t respect that, he’s the immature one, not you. He must have a friend who he’s not sleeping with who he can gossip about sex stuff with, right?

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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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