How to: Plan a Date in New York City

When I moved to New York in June 2014, I was largely a fish out of water. Still fresh out of college and having only lived in Deep South states, I was excited—however a tad overwhelmed— to begin the postgrad journey in this place of opportunity. (See here for the cliff-notes on how my feelings toward this “opportunity” have ebbed and flowed.)

After the first few months, I felt somewhat adjusted. I was “making it” in New York. Then, I went home for the holidays and got the age-old question from friends and family: “So, been on any dates?” I remember my response going something like, “No, not really. Honestly, dating is so different in New York.” Then they’d say, “Oh really, how?” And all I could come up with was “Well, I don’t have a car.”

Insert eye roll and facepalm. Looking back, that was a terrible excuse with a capital E.

Actually, I’m going to give myself some slack, but only for the remainder of this paragraph. I was new to the city and honestly still fairly new to dating. Heck, I’m still “relatively” new to dating, but I’ll end that potential rant before it derails the credibility of this post.

Okay, back on track. I’ve lived in New York almost four years and have dated some throughout that time. Sure, certain things may be different here than in other places, but I submit to you that it can be done and in exciting fashion.

Below, I’ve listed a few date options to consider. Note that some of these have been crafted by personal dating experiences, and others come from things I’ve done with friends but can also work as a date.

Before we get started...

Before we get to the date options, though, let me give you a little bit of strong encouragement for how to frame things. It’s easy to slide past these to lessen the blow of possible rejection, but that’s not the most respectful thing to do—so don’t do it.

Communicate intent: If you want it to be a date, then call it a date.

When planning, ask yourself, “Will this create a space for us to get to know each other better?”

And if it’s a date, as you’ve indicated above, then you pay.

THE DINNER DATE //

While I’ve come to learn that dinner dates can sometimes feel more like an “interview” than a “date,” this setting is usually the most comfortable, especially if it’s a blind date.

It’s safe to assume that people know how to navigate menus and waitstaff. Being in a public space and having someone basically interrupt you from time to time can help take the pressure off.

After all, “it’s just dinner.” There’s a definitive end, which can provide a nice, respectful exit—if necessary—upon receiving the check. You walk to the subway or snag a cab, and it’s over.

Uptown: For a somewhat casual (but still nice) dinner date, go to Bella Luna. It’s an Upper West Side staple that recently reopened with much excitement. Afterwards, I suggest grabbing dessert across the street at Milk Bar. And, if it’s nice out (and if the date is going well), suggest walking a bit. You can walk south along Central Park towards the Museum of Natural History, which conveniently also has a subway stop. (Alternate UWS dinner spots: Land, Lokal and Maison Pickle)

Downtown: If you want this, then you’ll have to find some other source. Just kidding. I recommend having dinner at Jeffrey’s Grocery, Claudette, or Tacombi (the one in NoLita).

THE MUSEUM DATE //

If you’re not into art, I recommend trying every dinner recommendation listed above. That should buy you some time until I do another post like this. Admittedly, though, I wasn’t a “museum guy” either until a few years ago, but they do make great date spots. (Note: That’s not the only reason I like them—art is cool!)

Uptown: I recommend going to Cooper Hewitt. It’s not as overwhelming as The Met (from an “I’m on a date” perspective), and it’s interactive. It’s also part of the Smithsonian “family,” which is fun, ha!

Try this as a Saturday late morning or early afternoon date, for it’ll flow very nicely into brunch or coffee at Bluestone Lane, which is just across the street.

Alternatively, if you want The Met, then I suggest going to Met Breuer on a Friday evening. It’s housed inside the old Whitney building and isn’t super packed on Friday nights. (Most people are actually hanging at their restaurant instead of looking at the art.)

Downtown: Initially, I’d say go to The Whitney and then walk The High Line. But, you can also find a great deal of fun hopping around the various smaller galleries in Chelsea. If you choose this option, grab coffee at The High Line Hotel, and then start out on your tour. They also have a pretty cool “neighborhood map,” which can provide some additional options as part of a Saturday “day date.”

WHAT'S THE DEAL //

You might ask why I wrote this. Well, I’m currently not dating (see here), and I like planning. If any of y’all has experiences after taking me up on anything mentioned above, please feel free to comment below or email me directly. I’d love to hear from you! 

Ultimately, the city is a fun place to explore. Yes, it’s crammed and bustling; but with a little creativity, dating (or even just getting to know someone) in New York can be a great, low-pressure, and mutually fun (and respectful!) experience. No car required!