The Debrief: From Boston to New York City in 10 Steps

I’m really doing it—I’m moving to New York City next week. When I made the announcement, I asked for advice about getting back into dating after I move. Since then, I’ve had some great conversations with friends about what to do and how to do it. Here’s some of the wisdom I’ve received. Thanks, friends!

  1. Move quickly. There are a lot of people, and none of us have a lot of time. Once you start chatting with someone (on OKCupid or Tinder or somewhere else), it can quickly shift to scheduling a date, for the next day even. In grad school I found myself needing to make social plans weeks in advance, so I can’t quite picture how this might work, but it does seem efficient.
  2. Start light. A first date should be under an hour. Meet up after work, in the early evening. To quote my friend: “You want to avoid that feeling of, oh, it’s after 9 p.m., let’s have sex.”
  3. Shed the sex-shaming. One person said to me, if you’re young and single and in New York City, have sex as much as you want to. I think that anyone should be able to have consensual sex without feeling shamed about it, and I also think there’s no shame in being young and single and in New York City and not having “tons” of sex if that’s not something you want to do.
  4. Know what you don’t want. Find comfort and confidence in setting boundaries with dates. If you don’t want to have sex, say that. See if you’re with a person who can hear your boundary and not push you, not guilt you, and will still want to stay connected to you in a way that is mutually desired.
  5. Stay open at first. Explain upfront that you’ve just moved, don’t want to jump into anything, but do want to meet people and connect. Try to avoid attaching yourself to one specific person while you’re still exploring different scenes. Meet lots of people and start building a foundation for yourself as a new person in a big city.
  6. Know where you’re at. How emotionally available are you right now? How much do you need another person to be emotionally available? If you’re looking to get deep with someone, what’s the response you’re looking for, and is that person going to be able to give that? Each person should also be doing enough of their own work to take care of themselves and access other sources of support, so if you do open up to each other emotionally, it’s more about exploring how you relate to each other than trying to address urgent needs.
  7. Know who you are. “They really dress up in Manhattan,” one friend said to me as she eyed my bright dress, frizzy curls and minimal makeup. “Don’t feel like you need to compete with that,” she continued. Stay yourself! Have fun dressing up and going out, but stay yourself. I know that’s going to be hard to do in the context of New York City standards and wanting to fit in, wanting to be noticed and included. I think part of me is really excited to experiment with clothes and makeup a little more, and another part of me is skeptical about balancing the pressure and the playfulness.
  8. Follow your interests. I’ve been told to join a sports team, attend Shabbat services and potlucks or go see live music. It sounds like a great strategy, to not just look for people to date, but look for things I want to be doing in my life. And I’ll add dance parties to that list, of course.
  9. Be outgoing. People like people who like them. Even when chatting with someone you don’t really know yet, online or in person, add in some of the flirtatious stuff to show that you’re interested, maybe, potentially. You need to keep the conversation going somehow in order to even get to the point where you can really get to know that person.
  10. Make friends. Of the people you meet up with to maybe date, many of them you won’t end up dating. If it doesn’t work out, you might want to be friends with them. For me, it’s hard to balance this possibility with the advice to be flirty. Be flirty to put yourself out there, but keep it open-ended so you can be friends instead if you want to? How about just be yourself and connect with people and see what’s there?

Basically it’s really hard to get to know people sincerely. It’s hard to get past the having fun and checking each other out and dressing to impress. I hear that it’s even harder to form intimate relationships with people in New York City than in Boston, whether friendships or romantic relationships. There are a lot of people, and people are really busy. Social events tend to involve going out to do things, see things and get seen, which can make it hard to have some real time to talk and be vulnerable and intimate together.

But I’m going to try. I’m looking for friends, dates, colleagues and co-conspirators. I’m looking for relationships that can be energizing, caring, inspiring and not draining. I’m looking to continue learning how to be the best version of myself, and I’m looking to be present and honest with the complicated and tender parts of other people. Seeking human connection is not simple, but it can be fascinating and even fun. Bring it on. And keep sending me your suggestions and set-ups!

Thanks for being a part of The Debrief for the past two years! This post will be the last for me. A special thanks to David Levy for helping to launch this column, and to Kali Brodsky for moving it forward. Contact Kali if you have other ideas for what you’d like to see. And please check out my other blog, Sex Ed Transforms, and follow me on Twitter or Facebook to hear about future projects. I’m going to take a break from blogging for now, but I might just have something else going again in the fall. Be in touch!

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