Let Us Sex-plain: Should I tell my roommate I have feelings for him?

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 had a great first date, and I can see us together, and I’m pretty sure he feels the same way. I’m not going to cancel my other four dates this week because that would be overly optimistic, but I’m a walking case of FOMO, and I need someone to tell me when to stop searching for someone better. How long should I keep making dates with other guys? How long before I should delete all my apps and suspend my dating-site subscriptions?

—David, West Village

David, do less. Even if you never see Good Date Guy again, delete at least some of your apps. Don’t go on five dates a week. If you’re looking for a relationship, this sort of frantic net-casting is not the way to go. Date with intention, and try not to make yourself crazy along the way. In the meantime, focus on seeing the guy you actually had a connection with for a second date. If things work out, you two can have a conversation about exclusivity down the line.

I’ve been dating a woman for more than a year, and we are pretty serious—or so I thought. She told me she met a man on the subway, and she gave him her number. Confused, I asked why. She said he seemed nice and they would just grab a cup of coffee. I don’t think any guy just wants to meet for coffee. She said she cares for me but is always looking for a new friend and feels I am overreacting. It’s made me rethink our relationship. Any thoughts?

—Andrew, New Jersey

I understand why you feel this exchange was odd, and you could be right that Subway Dude has romantic intentions, especially if your girlfriend didn’t say she was in a relationship during their exchange. But men and women can be friends, and the fact that your girlfriend came straight home to inform you about the encounter makes me think her intentions are pure. If she comes home after coffee and says they’re heading to a candlelit dinner, you can start worrying.

I have a huge crush on my roommate, and he sometimes acts like he reciprocates my feelings, but he’s also a genius and spends a lot of time in his room working on cool academic stuff. Any suggestions on how to get him to make a move? I’m afraid to do it myself in case he actually doesn’t like me and thinks I’m stupid (though he has said he’s amazed by how much history I know).

—Merzeen, Bronx

Maybe your roommate can take a break from his cool academic stuff long enough to fall in love! Don’t count on him to make a move; if you’re sure this is what you want, make the move yourself. Yes, it’s risky—he may not have feelings for you, and it could disrupt your friendship and living situation—but I think sitting around, wasting time when you guys could be flirting over historical facts is much sadder. Be brave!

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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.

By: Jillian Anthony