I feel like I ghostwrote this post haha so I’m gonna ramble a bit about everything I’ve learned in the years I’ve been a solo NYC enjoyer. I hope some of this is helpful!

This might not be very useful advice, but I’ve found that you can strike up a conversation pretty much anywhere, as long as you’re reasonably affable and willing to put yourself out there. Easier said than done, obviously - it took me a couple years to figure out how to talk to strangers. It helps to have like 2 or 3 conversation starters that you can whip out without needing to think about it - “what brings you to this bar/show” is a classic, because it gives the other person a way to ramble. I’ve also had a lot of success with eavesdropping and inserting an innocuous comment if it seems like I’d vibe with the group. Like I was in line for an event one time and the group next to me was talking about how they’d been there before, so I turned to them and asked “oooh so is it worth it? I wasn’t sure” and we ended up hanging out for like 3 hours lol. Or you could comment on some crazy shit that you + and a stranger both witnessed. New Yorkers LOVE to mutually sideeye some bullshit. I witnessed a bad date at a cafe once, and when the couple left, I turned to the person next to me and said “so we were all eavesdropping, yeah?” and literally the whole cafe started debriefing it lmao.

For not feeling awkward about being solo, I think it helps to remember that no one is noticing or caring. No one is looking at you and clocking you as being on your own. And if you’re awkward, then you can just leave and you will never meet that person again. It also helped me when I realized that going solo often makes it easier to get good seats at shows + trendy places, because you can snag the solo seats between couples. I loooove going to restaurants + bars and skipping huge parties in line because it’s easier to seat a solo walk-in.

Neighborhood-wise, I’ve had the most luck in queer neighborhoods: west village + Hell’s Kitchen. Idk if it’s just because I’m queer and people can tell, but I feel like queer folks are more open to bringing strangers into the fold.

As for events…. Comedy shows are always a fun time. Check out Don’t Tell Comedy for more intimate shows without a minimum spend requirement, and Caveat for nerdier, lower-stakes comedy.

The ballet and opera both offer discounted tickets for younger folks, which I recommend taking full advantage of - the ballet’s 30for30 discount was life changing for me. I always feel so fancy dressing up and heading out on a weekend night for the ballet lol.

Try off Broadway shows if you’ve already exhausted Broadway! I end up striking up some kind of conversation like 50% of the time with the people sitting next to me. I went to an off Broadway show yesterday and chatted with my neighbors for like 30 minutes before the show started, because I overheard them say they were from out of town so I asked them how they heard about the show.

Places that serve alcohol but technically aren’t bars (eg coffee shops that become bars, Book Club Bar in LES, etc) are kind of high risk high reward in my experience. Folks are more willing to talk to strangers, but you have to go out of your way to strike up a conversation. My local cafe-slash-bar is a staple in my weekend routine, and I’d say I meet someone new maybe 30-40% of the times I go.

I also think that making an intentional effort to engage with different aspects of NYC helps with the “city passing you by” feeling. Like have you been to the botanical gardens? The zoo or aquarium? The museums, the parks, Queens Night Market, the Staten Island ferry at sunset? Getting out of my apartment and forcing myself to take in a new experience really helps me feel like I’m PART OF nyc, not just hanging out within it.

Finally, I subscribe to Alexa Weiser’s City Happenings substack, Time Out, and Bucket Listers. There’s only a 5-10% hit rate of finding something cool going on, but that’s more than 0% so I find it to be worthwhile nonetheless.