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 have a very specific kink that I want to pursue, but I’m not dating anybody right now, and I don’t want to weird out randos on the Internet. How do I find somebody to play with?
—Sandra J., New Jersey
Here’s the thing about randos on the Internet: They want to be weirded out. Some of them are specifically there to explore their own kinks and would be more than happy to oblige yours. In fact, there’s an app called Whiplr that can connect you with playmates. You can list your specific category of kink (materials, behavior, etc.), your sexual orientation (which can be fluid) and even your safe word. Do some sleuthing on meetup.com, check out the Spanking Club of New York (completely real), or look up one of the many sex parties that happen in the city.
With everybody on dating apps, where should single guys go to meet cute, successful single girls in real life? Do I have to go to a Meatpacking District nightclub (ugh)? I’m into professional women but have a hard time finding them out at the bars.
—Steven C., downtown Manhattan
This is a really common complaint for many single people in New York—we’re constantly eye-fucking each other in public but can’t seem to actually meet. My foremost piece of advice is terrifying to many: Approach people you’re interested in! What I mean is that if you’re in a social setting where it would be appropriate for one stranger to strike up a conversation with another, go for it. (Do not take this as a free pass to accost women who are clearly trying to go about their day without being catcalled every five minutes.) Yes, you can meet people in bars, but you can also meet them at a bookstore, dance party or bodega. You won’t strike gold every time, but you never know who you’ll click with just by having the courage to speak up.
After a third date with a girl, she invited me back to her place. After some foreplay, I went down on her for a while and went to grab a condom. She said she didn’t want to have sex, which is fine, and I didn’t push her, but then she didn’t return the favor. What’s the best way to deal with a situation like that?
—Joe D., Brooklyn
Ah, Joe, how refreshing to hear this tale from a man! Ask any of your straight female friends how often this exact situation has happened to them. I’m sure you’ll get an earful. Sex isn’t tit for tat, but in a hookup setting, usually both partners are hoping to get off. I think the best way to deal with a selfish lover, or any lover, is to directly ask for what you want. At that point, if they say no, you shouldn’t push the matter. But it doesn’t hurt to ask, and nobody says you have to see them again.
