1. Russ & Daughters + Landmark Sunshine (Lower East Side)
You might’ve heard of the famous “house that herring built,” a fixture of the Lower East Side for 100 years now. Incredible bagels, lox, and all the sort of stuff the Lower East Side has been consistently famous for. As depicted in this episode of Louie, a great place to go at weird times. (It actually closes at 8, but could be a cool thing to do for a late lunch or early dinner.)
Following Russ & Daughters, walk a block west and go see a “film” at the Landmark Sunshine Cinema. It is very “Cinema” like, a must for anyone who talks about movies too much and enjoys feeling cultured.
Estimated Price (For 2): $60
Perfect For: Couple that thinks they’re a lot more interesting than other couples.
2. Chicaklicious Dessert Bar (East Village)
Like many a dude, I’ve found that the key to many a woman’s heart is a dazzling desert game. Chickalicious is a “dessert bar” — you go there, wait outside for a little bit and make small talk with the couple in front of you, then sit down to deserts that taste as good as they are pretentious.
It’s price fixe menu — it comes with an appetizer thing, petit fours, and the desert of your choice. When I went, I got this cheesecake that I’ve had no choice but to bring up every time the subject of cheesecake comes up in conversation.
Estimated Price (for 2): $40-$60
Perfect For: Couple still in the “impress each other” phase.
3. Chinatown Walkaround (Chinatown)
Cool thing to do during the day. Get some bubble tea, hit up Joe’s Ginger, have great conversation about how New York City is great but simultaneously terrible — nothing says that quite like Chinatown.
Estimated Price (for 2): $35
Perfect For: People trying to force themselves into a relationship.
4. Bonnie Slotnick Cookbooks (West Village)
You could easily go to any restaurant in the West Village, and there’s 95% chance it’ll be great. But if you’re looking for something a bit “different” (thus building you up to be an adventurous, interesting, dateable person), go to Bonnie Slotnick Cookbooks. It’s a store run by this very nice, locally famous woman who sells all types of cookbooks.
The store hours vary by week to week, which you could check out on her website. Overall, this is great place to walk around, get slightly nervous about the more expensive cookbooks, and then buy it because it’s a long-term investment and you don’t want to look cheap.
Estimated Price: $10-40
Perfect For: A scene in an “it” indie.
5. Comedy Club Central (Greenwich Village)
The default option here is to head just south of Washington Square Park and visit the Comedy Cellar — it’s the place featured in the aformentioned “Louie,” and is definitely the premier comedy club in the jokey-joke hotspot that is Greenwich Village.
That said, I’d encourage you to walk the streets around the Comedy Cellar — all over MacDougal and Bleecker you’ll have barkers trying to get people just like you to hang out at their much lesser publicized comedy shows. What these shows lack in big-names they more than make up with in price and unique experience. They’re often free, you never really know what you’re gonna get, and the caliber of comedians are pleasantly unpredictable. If you want a real feel of the life of a comic, these are the shows to go to. (Translation: please come to my show.)
Estimated Price (for 2): $15 – $80
Perfect For: Couple perfectly content with people with no future calling them out on their shit.
6. Beauty & Essex (Lower East Side)
I haven’t been to a ton of “trendy Lower East side places that make for great instagram opps”, but I have been here and I must say that if there’s a place you want to spent half your paycheck on, it’s this place. The food is outrageous, it’s super hip (in the sense that the front is deceiving and doesn’t look like an actual restaurant, then you get past the entrance and suddenly it’s a Vanderbilt Mansion), and you’re very likely to overhear a ridiculous conversation from the venture capitalist seated next to you.
Estimated Price: $150
Perfect For: Keeping up a facade.
7. Ace Bar (Alphabet City)
Cool bar in cool up-and-coming part of the East Village. Has skee-ball and a bunch of other cool games. Drinks are cheap, as are the games, and your conversation could subsist entirely on increasingly flirtatious trash-talk re: your intense game of darts.
Estimated Price (for 2): $25-50
Perfect For: Date after awkward Tinder hookup.
8. Gemma (NoHo)
Gemma is the restaurant next to/is a part of the Bowery Hotel. The Bowery Hotel is where famous people often stay, so the crowd is very New York Hollywood.
Gemma doesn’t take reservations, but the dining room is pretty huge so there’s a decent chance the wait will be painless — non-existent. Gemma is one of those spots that makes it appear like you really know New York, something accentuated by the caliber of crowd. It’s also a lot less expensive than you’d think a place like that would be. Also a really solid place to grab a cocktail and appear to be glamorous.
Estimated Price (for 2, sans a super-expensive bottle of wine): $60
Perfect For: Young couples that are old couples.
9. Strand Bookstore (Union Square)
If you haven’t heard of Strand, the independent bookstore of all independent bookstores, this wonderful video of Paul Rudd & Amy Poehler will tell you all you need to know:
I go to Strand often, as it is a terrific place to maximize my pseudo-intellectual potential. There’s always couples in there trying to out-Foster Wallace each other, which is always great to observe — I’d say it’s just as solid a date place as it is a watching place.
Estimated Price (for 2): $0-$40
Perfect For: Couples who enjoy watching other couples that are on the verge of having giant arguments in public.