135 W Broadway, New York, NY 10013 / 212 374-1135 Rating - $$
The Man in Black in a pink house? Johnny Cash might not have felt at home in Tiny's but his music fits perfectly. A landmarked 1810 historic building where the servers wear aprons and it feels like a dinner club from a bygone era – Tiny's is the best kind of relic.
It has original tin ceilings, vintage wallpaper, salvaged wood panelling, and will make even the oldest soul feelyoung again. The dessert menu is the absolute highlight and full of whimsical creations. Ice cream sandwiches, smooth panna cotta and milk chocolate meringues all jostle for space.
With this many choices you'll have to work together to try them all. Or you could use it as an excuse to book a second date. Win, win.