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Let Us Sex-plain: Is he my boyfriend or not?

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!

I’ve been dating a guy since August. We have sex, we go out sometimes, and I’ve met his friends, but I don’t know if we’re in a relationship or not, and I’m scared to ask. I’m 23 and he’s 34, which makes it even more difficult. Are we dating?
—Ellen, Williamsburg

My general advice on having the relationship-status talk is to wait until you really need to know the answer, but you’re already there. You’re uncomfortable with the ambiguity of the situation, so ask him! You deserve to know, and hopefully he’ll give you a straight answer. If yes, you can rest easy and keep building your relationship. If no, you can make a choice to stay in the situation or move on. I wish the best for you, but I would be prepared for him to tell you that, in his mind, things between the two of you are more casual than what you’re hoping for.

I’ve been dating a girl for about a year now, and she only gets off when I play with her clit. I’m used to being with girls who can climax with me, together, but I now find myself taking a half-time break during sex and pleasing her before I continue to the finish line. Any suggestions?
—Nick, East Village

If you really are used to climaxing at the same time as the women you’re with, you’re lucky—like, statistically. Two thirds of women don’t come from vaginal sex alone, never mind in sync with their partners. Don’t treat sex like a finish line, especially if the goal is only centered around your orgasm. Get her off first before you do anything else. Mutually pleasure each other. Have sex in a position in which you can play with her clit at the same time, or have her take care of herself in the meantime. Or try a sex toy you can use during sex! I want to see a little more creativity, Nick.

I started dating a guy, and for the first month it was really great. Then we had a bad date where he was moody and barely touched me or looked at me. Now he’s creating major distance, recoiling when I try to kiss him and expressing no interest in sex. But he keeps telling me he wants to date me and talks about the future. What the fuck is going on? I can’t get him to clearly tell me what he needs.
—Michelle, Jamaica, Queens

A good month does not equal a good relationship. This man is giving you extremely mixed signals, and actions mean far more than words. He is showing you that, for whatever reason, he isn’t interested in getting closer to you, and you should pay attention to that. If you’ve tried several times to talk to him about what he’s feeling, and he refuses to clue you in, it’s time for you to move on. Save yourself the time and heartbreak, and cut and run—he’s showing you his true colors, and he can’t offer you the intimacy you seek.

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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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