Let Us Sex-plain: I want to casually date a guy who used to be my serious boyfriend

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

Illustration: Assa Ariyoshi

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!

After three years of long-distance dating, I broke up with my NYC-based boyfriend earlier this year. But I recently moved to NYC and he wants us to be together again. I still love him, and we’ve been hooking up, but I don’t want to let go of single life. I don’t want to stop seeing him, but I don’t think he’d be okay with casual dating. What should I do?

—Gill, East Village

This is someone you had a serious relationship with, who you still love. Sorry, but casual dating is off the table. You know you’re not ready to commit, so tell him that and stop leading him on. If you really love him, you’ll respect his emotions (and your own) and cut communication while you build your own life here. Enjoy it!

I’m online dating for the first time. I have a mild physical “deformity” that is not immediately noticeable in photos, though it is noticeable in real life. When is the best time to tell potential dates about it? Right up front seems weird (and I’m kind of uncomfortable talking about it), but it also seems deceptive to wait until we actually meet (I would want to know if the tables were turned). And please don’t say that the right guy won’t care about the deformity!

—Kim, Brooklyn<

This is a very personal choice, but since you say you would want to know this about someone before meeting in person, and since this is online dating, an easy solution is to add this information to your profile so it’s out of the way before you start talking to someone. I do understand that option could invite bad internet behavior or awkwardly probing questions from people, so perhaps you should share this information with your dates prior to meeting them (rather than with the many thousands of New Yorkers who will potentially swipe right or left for you). And okay, I won’t say it.… But I will say you deserve to be accepted and loved for who you are.

I’m a college student, and lately I’ve had anxiety about going on dates because there’s always this expectation of hooking up at the end. I don’t feel attracted to people I’ve just met, and I need to really like them before we get together. How can I be up front about my preferences without seeming crazy or like I’m trying to DTR too quickly?

—Elise, East Village

It’s fine to be hopeful for a hookup, but anyone who tries to make you feel bad or guilty for not wanting to have sex can fuck off. You can tell dates you prefer to take things slow and really get to know people before getting physical, or you can be so forward as to say before your date even starts, “I want to be clear I’m not interested in hooking up tonight.” That would definitely weed out people not worth your time! There’s no shame or compromise required here, and there’s nothing “crazy” about feeling uncomfortable sleeping with someone you met two hours ago. Spend your time with people who respect your wants and needs and genuinely try to get to know you. And trust yourself.

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Read previous weeks’ sex columns

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

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