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Let Us Sex-plain: Should I tell my ex’s girlfriend he’s a cheater?

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

Illustration: Marina Esmeraldo

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 broke up with my ex for good in August. He and I dated for three years, but after ending things, we continued hanging out as friends and would occasionally hook up. A week after our last hookup in April, he wasn’t being communicative. I confronted him, and he told me he’d had a girlfriend since March. Should I message her about it and let her know she is dating a cheater?

—Molly, Astoria

No. Your relationship with this man is over, though it seems you haven’t fully accepted that. You have nothing to gain from either telling this woman about his apparent indiscretions (you can’t be sure you know the whole story) or continuing to communicate with him while you’re still emotionally tied to him. Cut off contact for 30 days at the very least. After that, if you still want to talk to him, you’ll soon find out whether or not you have a real friendship with him when sex isn’t involved.

Do men find it uncomfortable to date a woman who is a bit aggressive in knowing what she wants? Being a native New Yorker, I have a natural hustler attitude. I feel as though it’s not considered feminine.

—Michelle, Bronx

At one time, voting, working or getting an education weren’t considered to be feminine. There have been many aggressive, bold women before us who knew exactly what they wanted and went for it. So join their ranks, keep hustling hard, and embrace your drive with pride. There certainly are men out there who will not be comfortable dating a woman who has big dreams, but they’ll only hold you back. So seek a man who supports and even pushes you to reach your goals, and don’t give the rest of them a second thought.

I’m with a woman I want to marry, but when she is around men who like her, they somehow end up making jokes about me, and it makes me feel insecure. She defends them every time and says the joke is funny. She also believes I should be fine letting her have lunch with a man who I feel likes her. Should I stay or go?

—Edward, Crown Heights

I don’t have your partner’s viewpoint to draw on, but you need to work on your own self-confidence. You sound jealous, defensive and possessive of your girlfriend. No partner has the right to tell their significant other what they can and cannot do, and respectful boundaries should be reached through discussion. Your girlfriend can have platonic relationships with men, as you can with women. Unless you genuinely think she’s cheating and you want to confront her about this, you need to face your deep insecurities if you want to stay with this woman. And maybe try laughing at yourself now and then! Because unless your girlfriend is simply cruel, she’s probably asking you to please lighten up when she’s “defending” whatever jokes these men make.

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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