hopscotch

Get a red stripe and some crazy good jamaican food at this super-cool & uniquely trendly spot. 

Pro Tip: If you're both hungry try the Jamacian sampler for two.

Pro Tip: There's a record store attached to the restaurant. If you're big on music- you can earn some points by showing off your knowledge after dinner or before in case you have to wait. 

Next stop: Cocktails. Get you're head spinning with a round or two of stiff coctails from the always fun Pegu Club.

Spend some time wandering the this timeless department store. Stop at the Lower Level cafe for tea sandwiches, sweet pea soup and great people watching. 

The definition of chic, Fivestory is a classic concept store. Great for shopping or browsing, this townhouse does not dissapoint. 

Grab a drink at this old-school jazz bar that serves bar bites and classic cocktails with a twist. 

Nothing says NYC like old world Italian food. Elio's is an UES staple that won't dissapoint. 

Start at the impeccibly decorated Jean George restaurant Perry St. Make sure you dress well to avoid standing out negatively in the beautiful surroundings (collared shirt + formal shoes a must).

Pro Tip: Order a bottle of champagne or white wine in advance to set the mood.

Wander over this secretive cocktail bar. The drinks are second to none and the setting is incredibly intemate.

Pro Tip: Try to stick to 1 or 2 cocktails since they're stiff and it's late.

Feast on some of the best Chinese/American food in town. 

Check out this hidden restaurant/bar for some great music, beers, and possibly tacos. The sweet spot is ~ 10-12 for good vibes before heading out to someplace more late night.

Turn the volume up at Haus and let the night take you where it wants.

Start off with a cocktail and oysters to ease into things. If things don't go well- no big deal, tell her you've got to get up early or something and move on. If they're going well- grab the check and tell im or her you've got a surprise in store. 

Walk over to this romantic cocktail spot and, if things are going really well, get the Chef's tasting (a relative bargain at $65.00).