Let Us Sex-plain: Should I keep sleeping with my boyfriend if we're on a break?

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!

My boyfriend and I are on a break because he says he needs time for his internship and “to make our future better.” Do you think it’s okay to still have sex with him, or is it better to explore other options?
—Jessica, Astoria

Oh, dear. “On a break” tends to mean “I’m breaking up with you but leaving it open-ended so you can still be there for me when I need you.” From personal experience, I advise you with gusto: Save yourself a lot of pain and confusion, and walk away now. That means no contact for at least 30 days and definitely no sex. I heard something once that I try to live by when it comes to dating: “It’s either fuck yes or no,” meaning unless you’re ecstatic to be with someone, end it. You’re getting a big no right now. The sooner you move on, the sooner you’ll find the fuck yes.

This guy I’m seeing is really great, except for one thing: He makes the weirdest face and grunting noise when he comes. How do I say something about it without offending him?
—Marla, Tribeca

Not to belittle your issue, but I can’t help but giggle reading this question. We’ve all dealt with this, right? The thing is, unless you’ve filmed your own “O” face, you don’t know just how awful yours might look! My point here is not to make you paranoid but to remind you to take this quirk with a grain of salt. If you’ve ever had an orgasm, you know the last thing you’re thinking about is the fact that you’re making the same sound (and face) as an orangutan giving birth. Even if there were a way to train yourself to be more aesthetically pleasing when coming, that would take a lot of fun out of the whole thing. Let your man enjoy his release, and look the other way—maybe literally—on this one.

This hot guy I’ve been hooking up with wants me to pee on him, but I’m really, really pee shy. I tried doing it once in the bathtub, but no luck. Any tips?
—John, Bushwick

Carrie Bradshaw once asked, “To pee or not to pee?” And apparently people are still wondering. Have you tried drinking four cocktails in an hour? Every time I do that, I could pee literally anywhere. Seriously, urine is basically sterile, so water sports aren’t as “dirty” as they may seem. If you want to do this, natural diuretics like coffee or alcohol could aid in the, um, process, as could simply turning on some running water, closing your eyes and concentrating. I think the real issue here might be your trust level with this dude. Get to know him more in and out of the bedroom, and you might feel more ready to go chasing waterfalls.

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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