Let Us Sex-plain: How long do I wait to tell my new partner about my awful breakup?

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 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 just got out of a roller coaster of an eight-year relationship that ended in a far from ideal manner. What’s the best way to dip my toes back into the dating scene, and when do I (should I?) bring up to the person I’m seeing exactly how bad the situation I left was?—Shar, West Village

If you just broke up, and it was as awful as you’re letting on, you’re probably nowhere near ready to date. So forget all that. Focus on your friends, your own passions and doing whatever the hell you want right now, and see a therapist to work through the lessons you’ve learned from your long-term relationship. Take as much time as you need, and when you do feel whole and ready to see other people, leave exes entirely out of the conversation until you’re certain this is someone you really want to get to know (that’s the third date, at the earliest). No need to bring up the past right away when you’re looking to the future.

My boyfriend and I have been together for two years, and the sex is generally great. The only issue is that upon starting the act, it’s usually pretty painful, even with lube. I tell him to stop when it hurts, and we try something else. Are there tips and tricks I can try to make sex more enjoyable? —Megan, Bushwick

If insertion is usually painful, I’d suggest you see your gynecologist (medications could affect how you feel down there, as well as possible inflammation, injuries, STIs or even psychological issues). But some practical tips: Spend a lot of time on foreplay, as women can take 20 minutes to become fully aroused (men can take half as long) and create natural lubricant. Oral sex is a great kickoff! If this has to do with your partner’s larger-than-average size at all, try different positions that may be more comfortable for you (if you’re on top, you can control depth and speed), and be sure to fully relax before engaging in sex (take five minutes to breathe and meditate). Most importantly, try to be in touch with what feels good to you. Keep exploring!

My girlfriend has taken to putting on a certain podcast every time things are becoming intimate in the bedroom. While we have enjoyed listening to it together in the past, I really can’t get “in the mood” with Marc Maron talking in the background. How can I say that I enjoy this podcast but just not during foreplay?—Joshton, Williamsburg

Maybe she has a thing for his gruff voice? Because I can’t really imagine getting off to interviews with Randy Newman or David Remnick, two recent guests on WTF with Marc Maron. Gently say, “Having a podcast on is a little distracting for me. Can we try some music?” Or, make it sexy and say you want to hear every sound she makes. If she’s a reasonable partner, she should be pretty understanding!

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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

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By: Jillian Anthony

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