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Illustration: Assa Ariyoshi

Let Us Sex-plain: It bothers me that my gay partner used to sleep with women

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

By Jillian Anthony

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’m in a long-distance relationship, but whenever I try to make plans for us to see each other on the weekends, he finds all sorts of crazy excuses that he’s too busy. We’ve only seen each other six times in the last year. What do I do?

—Simone, Chelsea

You’re dating someone who either does not want to be in this long-distance relationship or actually cannot be, due to his schedule. Depending on just how long-distance you two are, six times in a year may not be so bad. Otherwise, I’m not sure why someone would make up “crazy excuses” not to see someone they’re in love with. Don’t prolong this: Break it off.

I’ve never had sex with a woman, but my partner of a year has (only to appease his parents, who at the time were very traditional). It really bothers me. I’m not a misogynist, and I understand that people explore their sexuality. However, my partner knew that he was gay, was not attracted to any of his girlfriends and was having sex with them anyway. This feels like deception to me, and it makes me worry about the trustworthiness of my partner.

—Ishkan, Chelsea

Sexuality is so complicated, and it’s even more confusing when you have parents you’re actively trying to please and appease. It may not be the most forthright choice to have sex with a women when you are certain you are gay, but we’ve all made mistakes in past relationships. I presume that your boyfriend is now out, and openly with you. Don’t hold decisions over his head that he made years ago, before he even knew you. I would certainly not want to be judged as the person I was 10 years ago, and I bet you wouldn’t either. If you ask him to elaborate further on the choices he made at that time, perhaps you’ll feel more empathy for him.

I’m 27, gay and have never orgasmed during sex. I still find sex totally pleasurable without coming, but I feel like girls get put off when they can’t make me come. It makes it super awkward no matter how much I reassure them. Do I have some weird problem that nobody else has, and how do I broach the subject with my partners? Or do I just fake it?

—Shoshana, West Village

Do not fake it. This teaches partners that they are pleasing you when indeed they are not, and they will keep expecting you to come forever more! You’re not alone. Although I don’t advise you to give up completely on orgasming during sex, I would suggest being really frank with women about your circumstances and ask them to please not put any extra pressure on you or themselves. Then just enjoy sex! Keep experimenting with different positions and toys, but remember that sex is definitely not all about the end-game. You will find a partner who understands this.

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Photograph: Shutterstock

Let us sex-plain

Sex and dating

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


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