Online Dating Tips for New Yorkers

By: Jess Downey |

Internet LoveI’ve been online dating since before online dating was cool. You know, when you had to use excuses like “we met through a friend” because you didn’t dare admit you met from the internet. And, because I’ve moved around some over the past decade, I’ve ended up dating via the interwebs in various cities. So I can tell you that while the gist of internet dating is the same, there are certain things that vary from place to place. Here are a few tips for online dating designed especially for our New York City readers.

Pick a place that’s neutral and preferably close to public transportation for the first meeting

There are millions of places in New York City to have a first meeting and one of the hardest parts is picking where to actually meet. I know it seems like picking a place near her would be more gentlemanly, but there’s no way to do that without giving away where she lives. It’s easier to share the neighborhood or general area where you both live and then pick a spot in between. Save the hot spots in offbeat locations or your awesome local bar for dates later on down the line.

Don’t meet too late

New York is a city of night owls. But meeting a person you’ve never met at 11:00pm is still a big no no and still sets a certain tone for the date.

Talking on the phone isn’t necessary

Unless you feel really strongly that you should talk on the phone, skip it and just plan the first meeting. However, do exchange numbers so you’re able to find each other or in case you need to cancel.

Don’t meet at a heavy populated area (Union Square, Times Square, etc.)

I love Union Square and I think it’s an awesome date. You can walk around and there are tons of bars and restaurants nearby. But there is nothing worse than being already nervous to meet a total stranger and then having to work through a crowd of people to hopefully find the random corner he’s/she’s standing on. If things go well, you’ll have plenty of time to stroll the farmer’s market hand-in-hand.

Don’t meet with groups or while you’re already out

Unless you’re using an app specifically designed for it or you’re both looking for something casual, don’t send a text to the person you’ve been messaging on a dating site and ask them to meet up when you’re out with friends. It’s just not cool.

You might meet (or talk to) the same person as a friend or someone you know

When I first moved here I met up with a gal that I knew from a writing gig. We were chatting and I told her about a guy I recently met from a dating site. Turns out she had met him earlier that year. It was a little weird at first, but then I found out it’s a pretty common thing in New York. Obviously it can get a little tricky if you’re dating the same person as a close friend, but try not to get too weirded out by it or let it ruin friendships or potentials.

If you’re not picking up the check be sure to pick something in the mid-price range

I know, I know, talking about money is so not romantic. It’s always a good idea for the guy to pick up the tab on the first meeting, but sometimes the guy will ask the gal to pick a place (so it’s easy for her to get to). Whatever the situation, if you’re not the one who is paying the check at the end of the night, don’t pick some place outrageously expensive.