A seasoned dater in NYC knows that a good date works like a good game of chess--things are unplanned, but the moves are never unforeseen. You must appear spontaneous, but think eight steps ahead. So, when all you really want to do is stroll the idyllic paths of the Highline Park and kiss your new romantic antic, don’t take them straight there--take them to the spots below that (whoops!) just happen to be near the High Line. High Line Park information, maps, entrances, and hours here.
NON-DINNER DATES:
Chelsea Art Galleries: Whether you’re the brow-crumpling, pacing type, or the I-giggle-at-uncomfortable-sculptures type, galleries are always a secret weapon in the dating world. Everything’s a conversation starter, and when there is silence, it’s okay because you’re looking at art--especially the avant-garde, mind-slicing work that is often showcased in the ‘hood. Chelsea’s gallery district is best enjoyed as a unplotted meander, but if you’re obnoxiously anal-retentive, you can check out the general borders and gallery schedules here. Roughly between 21st & 27th St., bordered by 10th and 11th Ave.
Kayaking on the Hudson: Once you’ve properly Facebook stalked your crush and established that you would get points for being adventurous--take them kayaking on the Hudson! Calling it “kayaking” is a stretch--they cordon you in at Pier 40 and you splash around in a kayak--but it’s still an adrenaline pumper. When you’re done, take a romantic stroll through the West Village and--”Oh look! the Highline’s right here. Wanna go up?” At Pier 40, at the very western limit of Houston St.
Upright Citizens Brigade: Only go here if your date likes to laugh. And if they don't, our suggestion for a great date is to go back to their place and get chopped up and dissolved in their bathtub. In any case, quality improv shows have been proven to lead to increased amounts of leg-brushing and tongue-kissing. Just make sure to go to an early show so it’s out before the Highline Park closes at 10.307 W 26th St.; 212-366-9176
DINNER DATES:
Blossom Vegan Cafe: If you're going on a hot date with Jessica Rabbit, take her here. The food is incredible, and it’s fresh and healthy by its very nature. So fill up on feather-light vegan food so you guys can feel guilty about other things later.
187 9th Ave.; 212-627-1144
Socorrat Paella Bar: Paella is a perfect metaphor for love...fluffy on top, with a delicious, crunchy crust on bottom. Okay so maybe not the best metaphor. But it's delicious. And unique. And Socorrat does the best in town. So when the sun's setting and you want to let the bons temps rouler, guess what's right nearby? 259 W 19th St.; 212-462-1000
The Cookshop: This spacious, relaxed spot is great for people with taste buds and taste. The food is greenmarket inspired (thus seasonal) and is prepared rustic-style using things like rotisseries and wood ovens (whoa). Totally charming, but unpretentious--exactly how you want to appear until your date gets attached and starts calling too much.156 10th Ave.; 212-924-4440