I spent the month before I went to college deciding whether to break up with my high school boyfriend. We still liked each other, but he was going to Miami and I was going to New York City. My biggest concern? I was worried that having a boyfriend would make it harder for me to make friends. I was literally worried that people wouldn’t like me as much if I wasn’t “available.” (File under: internalized misogyny.) We didn’t break up in August, but by November I was in the midst of a very messy transition from that high school relationship into what turned out to be a hell of a relationship with one of the guys down the hall. And then two years later I got out of that situation and tried to start dating again.

That was the last time I lived in New York City.

Now I’m going back.


Me on the train to New York

I’m moving back to New York in April, for a great job that I’m really excited about. I’ve been in Boston since I graduated from college in 2007, so that’s almost eight years and all of my “adult” life so far. In the past year, I’ve written about going through a breakup, being 29 and single, coping with a concussion and not having sex. Once I recovered from the concussion, I entered a period of intense work writing my dissertation. All of that, combined with this great Boston weather disaster, has left me feeling isolated and lonely and missing my friends, even the ones who are supposedly right around me, in Boston. It also means that I haven’t been dating, like, at all.

And with only five weeks left here, and a ton of work to finish during that time (ahem, dissertation revisions), I’m not going to start dating quite yet.

This time when I move to New York, I’ll be single. Single and, to be frank, interested. Looking. Open. I’ll want to start dating. And, oh my goodness, I have so many questions. I’ve divided my questions into two categories—questions about dating in a new place, after any kind of move, and questions about dating in New York specifically, compared with Boston.

On dating in any new place:

  • Settling in: How do I know when I’m “ready” to start dating? How do I avoid plunging into something new as a way of coping, instead of connecting? How do I know when I’m settled enough to have a steady foundation?
  • Remaining open: I know I feel interested in dating, but it’s not like I’m looking to launch a relationship right away. How do I make sure I can meet and flirt and explore and also remain open to lots of possible shapes my life could take, and lots of different people who could enter my social and emotional worlds? How do I keep my options open while actively exploring those options to figure out what they are?
  • Kissing-and-telling: When I went to college I was worried that being in a relationship would make it harder to make friends. Now I’m worried that not being in a relationship, that actively looking to date, will make it harder to make friends. How do I avoid getting caught up in drama or making enemies at the very time when I want people to like me and take me in as one of them?

On dating in New York City:

I could keep listing more and more questions coursing through my mind, but I’ll let you get started with these. As always, I welcome your advice in the form of public comments, personal messages or your own stories to share in response to these thoughts. Anything you have to offer is much appreciated!

Of course, I can hardly continue to be JewishBoston.com’s dating columnist if I’m not living in Boston. I’ll keep The Debrief going through March, so contact me ASAP if you have a story or question you want to submit. Also, JewishBoston.com is undergoing some changes itself over the next few months (a big redesign!), so feel free to submit ideas for content you’d like to see on the site. Lastly, please follow my work on my personal blog, Sex Ed Transforms, if you want to learn about future projects I undertake. Maybe I’ll even share some New York dating stories, once I’ve got a few.