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Let Us Sex-plain: How do I give my husband a threesome for his birthday?

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 went on a few dates with this guy, but then I had to work in San Francisco for a few months. When I came back, he had a girlfriend, but we met after that and hooked up. He said not to worry about his girlfriend and that he’d carry the guilt. I’ve stopped hooking up with him, but should I tell his girlfriend?
Sophia, Chelsea

This guy’s a cheater, and that’s something that’s going to manifest in his relationship in the future, whether his girlfriend finds out about your escapade or not, but it’s not up to you to be the bearer of bad news. Though I doubt this guy is losing any sleep at night over all that guilt he’s carrying, this isn’t your relationship, and you need to wipe your hands of this unhealthy setup and move on.

For my partner’s 50th birthday, I’d like to treat him to a threesome, but I’m not sure how to find the right person. I’m thinking an escort, but it might be better to find a more natural fit. Any ideas?
Angela, Tribeca

Ringing in 50 with a bang, I see. Leave the escorts out of it and meet someone the old-fashioned way: online! There are plenty of people looking to guest star in a couple’s fantasy on dating apps like Tinder and OkCupid or threesome-specific apps like Thrinder. You might find it exhilarating to hit on people with your partner. If the apps aren’t for you, hit the kind of bars where open-minded people might hang out, and approach them in a friendly yet flirty way. You may be surprised by how many willing participants you’ll find.

Recently it seems I just can’t get along with my partner of three years. We fight often, and lately, he’s started calling me names in the heat of the argument (e.g. fucker, psycho, idiot). I’m afraid this is a slippery slope to a verbally abusive relationship, but I also don’t want to give up on what we’ve built in the past few years. Can this situation be reversed?
Robe, West Village

You need to recognize that absolutely no one has the right to speak to you that way, especially within the context of a healthy romantic relationship. You’re right that this is a scary path, and you should hear what a professional has to say. Visit crisistextline.org to talk to a trained crisis counselor 24/7, free and privately, and keep an open mind. In the meantime, consider deeply what good parts of your relationship realistically still exist that you’re willing to stick around such negativity for, because it sounds like it’s time to move on, for both of you.

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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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