How to Deal With New York City Transportation on a Date

By: Jess Downey |

NYC TranspoI currently live in New York City, before that I lived in Chicago, and I honestly can’t tell you the last time a guy picked me up for a date. I know that might sound weird, but it has nothing to do with the “death” of chivalry or anything like that. It’s just because things can get a little complicated when you rely on public transportation and live in different boroughs than most of the people you date.  So here are a few tips on how to handle public transportation on a date in New York City.

Cabs are pretty easy. If you’re able to share do so and split the cost. If she decides to take a cab, help her get one and see her off.

Trains and buses are a whole other beast. Let’s take a look at a few scenarios, shall we:

Scenario 1 – You live/work on the Upper West Side off of one train, she lives/works in Brooklyn off a another train.

  • If it’s the first couple of dates, try to pick some place that’s easily accessible for both parties; aim for neutral.  It’s definitely acceptable to just meet at the restaurant or bar that way you don’t have to worry about timing things perfectly.
  • When the date is over be sure to walk her to her stop. Generally it’s a nice gesture to walk her down into the station and to the turnstile, but at the very least walk her to the stairs and then go your separate ways.
  • Once you start dating more, you’ll probably start to meet up in each other’s neighborhoods. In that case, I say meet at the subway stop or at whoever’s place and then head to your destination together.  At the end of the night all of the above stuff still applies (unless you’re staying over of course).

Scenario 2 – You live in Astoria, she lives in Brooklyn but you’re both off the same train.

  • This kind of works the same way as the above scenario only it makes things a little easier since you live on the same line; you’re just going in opposite directions. When you can, try to coordinate things so you’ll both end up at the stop around the same time and then you can head wherever together. And, at the end of the night wait with her until her train comes if you can. It’s a really sweet gesture that goes a long way.

Scenario 3 – You both live in Brooklyn, in the same neighborhood and off the same train (but different stops).

  • While this scenario seems super easy, things can get a little tricky; especially when you’re newly dating. If you’re stops are in close proximity (and the weather isn’t horrible), it’s never a bad idea to get off on the same stop so you can walk your date home. It also provides a very lovely atmosphere for a kiss, just sayin’. Be careful though; you don’t want it to appear like you assume you’re going home together. So maybe mention the fact that you can get off on his/her stop too.
  • If your stops are farther apart, still ride the train together – it helps to add some more time to the date and it’s just plain polite – and part ways at whoever’s stop is first. And obviously, if you live off the same stop consider yourself very lucky because you can easily just walk her home and skip all the above hassle.

Obviously there are a ton of scenarios, but even though figuring out how to work a train, a bus, or a cab into your dating life can be a total pain that doesn’t mean it can’t also be romantic. Just try to treat it like you would if you were dating outside the city with a car. If you’d usually see a gal home after a date, do the same thing. Or, you know, as close to home as New York allows.