Wollman Rink

This is the place where I learned how to ice skate.

The first time I went here also happened to be my first date with my current partner. I asked him if he wanted to go ice skating, and he agreed very enthusiastically, but failed to mention that he had never been skating until we were already on the ice. He would have been clutching the outer railing all day, but for some (albeit more fearful than romantic) hand-holding. We drank hot chocolate from the concession stand at the picnic tables and contemplated stealing the Zamboni for a joyride.

This is a cute little rink situated right next to a cute little pond in Prospect Park. It is both cheaper and significantly less crowded than most of the Manhattan rinks (Bryant Park is $2 cheaper if you factor in skate rental). Bring your own lock, and you can use a locker for free.