Let Us Sex-plain: I hooked up with my friend and now he won’t talk to me

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’m a bisexual man who hooked up with my bi male friend a few weeks ago. We agreed that it’d only be for fun and that we wouldn’t let it ruin our friendship, but he hasn’t talked to or seen me since. I tried reaching out, but I haven’t gotten a response. Is there anything I can do to fix our friendship?
—Jason, Bronx

You knew it could be risky to hook up with a friend. Who knows what’s going on in his head? He could have feelings for you, he could be pushing you away, or he could have something completely unrelated going on. Try to reach out by phone (not text—too many chances for miscommunication), and be clear that you care about him and your friendship and would like to discuss the situation. If he still doesn’t respond, sadly, you’ll have to let him go.

I had a few very nice dates with a man I met (let’s call him Guy 1), but he told me he wasn’t interested in pursuing things. Recently I bumped into one of his friends (Guy 2) at a party, and we had a great time, and I’m interested in him. Because I met Guy 2 through Guy 1, is it proper etiquette to ask Guy 1 about dating his friend?
—Sarah, Upper East Side

You know what’s proper etiquette? Living your life for you and putting your wants and needs ahead of a guy you barely know. It is extremely nice of you (too nice) to consider Guy 1’s feelings, but at this point, he’s already ended things with you, so you’re free as a bird to pursue other options. If Guy 2 wants to talk it over with Guy 1, let him. But you should ask Guy 2 out immediately!

Before I got married, my then-boyfriend often used to compliment random women in public as we walked hand in hand. We spoke about it and he stopped, but lately he’s started again. I think it’s disrespectful, but he says I’m just being insecure. I’m willing to divorce over this. Who’s right?
—Janice, Brooklyn

Even if your husband was out walking alone, it’s just plain rude to “compliment” women like this. I can’t say this enough: If you feel the need to comment on a stranger’s appearance, male or female, positive or negative, keep it to yourself. So, I completely understand why you feel disrespected by your husband’s behavior. His strange need to talk to women whom he finds attractive and whom likely have no desire to respond to him—an especially odd thing for him to do in front of his committed partner—is for him and a therapist to figure out. And you have a right to leave him if he can’t act right. Don’t let him manipulate you into discounting your own feelings.

Submit your own

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.

Read more
By: Jillian Anthony


larry g

No wonder the divorce rate is 50%. Husband compliments other women, time to call a divorce lawyer. Initial and proper response is counseling for this couple.