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Let Us Sex-plain: I want to date my friend’s sister

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 have a good friend whose sister I am very attracted to, and I’m not sure how to move forward. I’d like to let her know how I feel, but I don’t want to jeopardize my friendship with her brother. I also don’t want to risk not taking a chance with her. What should I do?

—Daniel, Brooklyn

A life well lived demands risk. If your friend is mature and trusts both his sister and you, he may well be happy about your revelation. But you have to consider whether you’re willing to potentially lose a friend in case he’s not. I say follow your heart (carefully), and make your good intentions clearly known, but definitely talk to your friend first so he has time to come around to the idea of you and his sis making out and stuff. Good luck!

Last year, my serious boyfriend ended our relationship, but we got back together after a month. I think I’ve done a lot to forgive and move forward, but I keep getting stuck on the fact that he didn’t ask me to be his girlfriend again. We’ve been very happy for months, but I still feel like he left me hanging by failing to give me this gesture to balance out his dumping me. Am I being unfair, or does he owe me something here?

—Cara, Williamsburg

I think you’re right that he got off easy. It sounds like you guys skipped over the really ugly stuff and went right back to dating. Good for you, and him, for moving on, but things won’t be resolved until you can let go of this resentment. Be honest with him about how you feel. I’m guessing he’ll admit that it just felt easier to sweep the breakup under the rug and pretend it never happened. But it did happen, and you guys need to talk about it! And if you want him to verbally ask you, “Cara, will you be my girlfriend?” I think that’s a sweet, easy thing he can do to help your (as yet undefined) relationship.

One of the first times my boyfriend and I had sex, I asked him to lightly choke me. He told me no, explaining that it “wasn’t his thing.” A year later, I haven’t brought it up again. Our sex life is great, but I feel this would open the door to another world I’ve experienced with previous partners. How do I bring it up again without sounding selfish?

—Adriana, Brooklyn

There is a vast difference in levels of trust between early sex with a partner and sex an entire year later. Your boyfriend might not have felt comfortable then, but he may very well be open to it now—and you should feel empowered to voice your fantasies! Say to him (with clothes on in a nonbedroom setting, so there’s less pressure), “Babe, I’d really like to try out some gentle choking in bed. Could we talk about some ways you might feel comfortable exploring this with me?” Hopefully he’s open to the conversation, but if he’s absolutely not into it, that’s his prerogative. At least try to find some middle ground!

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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