What are some good dates (lunch, dinner, day, etc) in NYC?
April 21, 2014 11:44 AM   Subscribe

In the first week of June I am going to NYC to visit a girl who I am hoping to woo. I have a pretty open window: the first day we are meeting is June 4th, and I'll be leaving that Sunday. Snowflake details inside.

This is a girl I have known for a very long time and, for various reasons, we never really "gave it a shot." She essentially wants me to court her, and as such I will go to NYC and take her on a series of dates (we only have it set up to meet on Wednesday, but assuming that goes well will continue to see each other). Either way, I'm not sure what to do! She has lived in NYC all of her life and while I have been to NYC a number of times, do not know the city nearly as well. I'm trying to figure out what might be a good way to spend that first day together... I know she doesn't like super heavy food, she likes lighter meals (think Japanese), that sort of thing. She does like desert, but I shouldn't go overly heavy I think. She's not a big museum person. I'm at a big loss of what sorts of restaurants might be good, what parts of the city might be fun to walk around... Further, as the long weekend progresses, I'm not sure what else we can do. We can only walk around so much, right? I know I'm not going to be able to "impress" her with anything in NY, so I think my main bar is to just have a lot of thoughtful, interesting things planned that will give us a chance to connect and enjoy each other's company. Oh, and she isn't really a drinker so potential ideas for non-alcoholic destinations after dinner would be really great. Maybe late night desert spots, cute cafes, somewhere romantic with a nice view, that sort of thing.

Any ideas?
posted by wooh to Human Relations (8 answers total) 4 users marked this as a favorite
What's your money situation like? That Sunday is the Tony Awards, and they sell tickets to the awards themselves. It's usually a fun night (Hugh Jackman is hosting this year), and I think it's impressive.
posted by roomthreeseventeen at 11:48 AM on April 21, 2014 [1 favorite]

NYC date things I am a little homesick for:

- Long Walks. The High Line is ideal if you want to go to a place for the purposes of walking, but honestly any old place in NYC that is convenient gets the job done.

- The Brooklyn Heights Promenade

- Loafing around in the grass in Central Park. The first week of June was invented for this purpose.

- The Brooklyn Flea or really anywhere food trucks and good people watching congregate.

- This is not NYC, but just a good sweet date suggestion in general: I like being taken out for spur of the moment snacky casual desert. This could be anything from a Cronut* to an Italian Ice off a cart in a park. I vastly prefer this to a sit-down "let's Go Out For Dessert" type of situation.

- Eataly?

- Poorly Kept Secret romantic bars I know about include Angel's Share in the East Village and The Campbell Apartment in Grand Central Station.

*I prefer Dough in Clinton Hill or Peter Pan in Greenpoint; there's also Bombolini on the UWS, but YMMV and I think there are tons of artisanal fancy donut places popping up everywhere now.
posted by Sara C. at 11:51 AM on April 21, 2014

Cha-an in the East Village hits a lot of your stated preferences (Japanese, lots of non-alcoholic beverages, dessert but not crazy heavy, good date atmosphere).

My advice to you, from one long time New Yorker to one not-very-familiar with the city, is to avoid anything remotely touristy or symbolic. Your sense of "smell" for these things is not going to be very sophisticated, so if you catch so much as a whiff of "hm, this might be a cliché NYC thing," I would advise that you steer clear.

Also, have you considered that since she knows you are unfamiliar with the city, she is expecting the "wooing" to be in the form of... I don't know... gifts? Professions of affection? Not so much with the actually taking her special places? I'm not really familiar with the "wooing" concept but I'm skeptical that she would expect you to swoop in out of nowhere and take her on special dates in a city that is foreign to you.
posted by telegraph at 11:52 AM on April 21, 2014 [2 favorites]

Free Shakespeare In The Park is performing Much Ado About Nothing that week; check the site for details on how to score tickets.
posted by ceribus peribus at 12:02 PM on April 21, 2014

Dude, if you are wooing her, you have to know what she likes. What does she like?
posted by amtho at 12:04 PM on April 21, 2014 [3 favorites]

Don't focus too much on the "NYC" part of this. What kind of dates would you take her on in your hometown?

Rent Citibikes and bike around.

Bring her flowers.

Sit in Central Park on a blanket and drink wine, bring a frisbee and a deck of cards and some books to read (share the Sunday Times if that's your kind of thing).

Find some live music - a chill, low-lit jazz bar, perhaps?

Cook a meal together (go to a farmer's market, pick out recipes, etc.).

Do whatever you'd usually do. Rock climbing? a movie? a concert?
posted by amaire at 12:13 PM on April 21, 2014 [2 favorites]

Free kayaking (there's a wait)
Picnic on the Highline
posted by brookeb at 12:13 PM on April 21, 2014

Definitely take a walk on the Brooklyn Bridge. It's free and you get an amazing view of the city.

I would say a picnic is a nice idea as well.

You could always try getting free tickets to a show (whether it be the Colbert Report, Daily Show, Late Show with David Letterman, Late Night with Seth Meyers, The Tonight Show with Jimmy Fallon, Who Wants to be a Millionaire, etc.). I know most native New Yorkers don't take advantage of how many shows are filmed in Manhattan or they don't think of it.

Most of all, I would just say keep up a high spirit and energy and show her how invested you are in this budding relationship and be receptive. It's great that you're being super thoughtful but I generally think that if two people have chemistry and compatibility they will imbue wherever they are with that romantic and tender ambiance they're created with each other. I kid you not some of the most romantic, warm memories I've had (and still are having) have been at places like a McDonald's parking lot and the subway.
posted by thischarmingirl at 12:20 PM on April 21, 2014

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