Let Us Sex-plain: Is the third date really the “sex date”?

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

Illustration: Assa Ariyoshi

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!

Is the third date really the “sex date”? Are guys I’m dating expecting me to sleep with them?

Meg, East Village

I did some research on Twitter and among my friends, and the short answer is: sometimes. Third-date sex is a stereotype, but in the millennial era, it seems realistic that people may be ready and willing to get physically intimate after spending a few evenings with someone. That being said, it really doesn’t matter what anyone is “expecting” from you. You decide when you’re ready to have sex, period.

I’ve become really close to one of my male friends in the past couple of months, and we both recently admitted we have feelings for each other. I was really excited, but now he’s telling me he doesn’t think he’s in the right place to start a relationship. He still wants to be friends, but how do I even do that? I’m in a lot of pain right now.

Becca, Prospect Heights

This man was clear that he’s not looking for the same thing as you, and right now, you’re not in a space to be friends with him. You’re hurting, and you deserve time to work through that without him sticking around as a confusing presence. Cut off contact with him for 30 days (it will go by fast, I promise), and work on things you’re passionate about. At the end of that month, give yourself permission to reach out to him if you still feel the need, but if the pain is still acute, give yourself even longer. A friendship can only exist when both people benefit from it, so you have to get past this first before you can get there.

I’ve explained to this guy I’ve been dating for the past month that our “relationship” isn’t working for me. He’s a poor college student, and I’m five years older with a successful career. Plus, the sex is bad. But he refuses to let me break up with him. It’s really throwing me off because he thinks he can just change to make me happy. Does this type of dedication mean something, or should I stick with my initial analysis that I’m just not that into him?

Shayla, East Village

If you’ve explained to this person it’s over, and he’s still not listening, you don’t have to be nice or accommodating to him anymore. Even if this guy has good intentions, it’s still really creepy he thinks he can just convince you to be with him. You’ve made your choice, so don’t second-guess yourself. Firmly tell him it’s over and you don’t want to hear from him anymore. (Oh, and don’t respond to his attempts to contact you; it takes two to have a conversation.) If that doesn’t work, block him everywhere you can, and move on. He’ll get the message—or lack thereof.

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