Firstly, do not under any circumstances take a first date to see a movie or broadway show. The whole point of going out is to try and get to know one another and sitting in silence for multiple hours is definitely not the way to do that. Also, I’d advise against a night club or crazy concert (yes, even if you’re a hipster).

Here’s a snazzy list of activities and places where you and your date are sure to have a fantastic time:

• Chelsea Market, 14th street & 10th Avenue
  The Chelsea Market is a block large indoor mini shopping center full of stores, bakeries, grocery stores, cute restaurants, and more. It’s the perfect place to start a date. You can stroll around for hours, and grab a casual bite to eat especially if the weather outside is less than desirable.
• Central Park Zoo, 5th Avenue at 63rd Street
  Everyone likes cute animals (I mean unless their some sort of psychotic animal killer). What better place to enjoy a fun and fuzzy experience than the Central Park Zoo. It’s casual, and is sure to get conversations going. Just make sure you’re okay being around kids because there’s bound to be some (no, not as part of the exhibits, jerk).
• Museum of Modern Art, 5th Avenue & 53rd Street
  If the person you’re on a date with is even a remotely intellectual person, he or she will have an appreciation for art. The MoMa is one of my favorite museum’s in all of New York City. If you’re not into modern art at all then perhaps you may want to try the New Museum or something classic like the Museum of Natural History.
• Governor’s Island
  One of the city’s newest attractions is Governor’s Island. Once used as a naval base, it is now a mecca of art galleries, live shows, shopping, eating and more. It’s the perfect place to go if you’re looking for a relaxing place to have a picnic and get away from the commotion of New York City. Offers stunning views of Manhattan and the nearby Statue of Liberty.
• Kenmare, Kenmare Street at Delancy Street
  If you’re more into the traditional evening dinner date, then Kenmare is the place to go.This is one of the most talked about new restaurants in the NoLita neighborhood for years. I can tell you from personal experience that the food is fantastic. Call ahead and make a reservation. Head to the ultra-lounge downstairs (if you can get in) for a couple of drinks and some music after your meal.

I hope this little list even remotely helped you. If it didn’t, then do what your heart says. Sometimes it’s better to just go with the flow and let things happen as they will. Trying to over plan something tends to usually backfire. Good luck and let me know how it goes!