This park has everything. Beautiful Monument? Check. Large Fountain? Check. Performance artists? double check. You and your date can soak in the sights and there is almost always some sort of political movement or performance going on. There are puppeteers and bubble blowers. Dancers and musicians. Maybe try your hand against some of the chess experts in the park.
Sit by the fountain or go and sit in the grass and relax. You are sure to have interesting things to see and talk about as you enjoy Washington Square Park. Park Website This park is lively at any time of day and is open til 1 AM. The people watching here is amazing!
One of NYCs hidden gems is the Cloisters. This beautiful museum is an extension of the MET dedicated to the art, architecture, and gardens of medieval Europe, and, like the MET, admission is donation based for NY residents. One dollar could get you admission for you and your date. Exploring the grounds is also a romantic idea. The Cloisters sits in Fort Tryon Park. Explore the old fortress or walk around in the curated gardens. This is a beautiful place to explore trails or sit and cuddle while looking out over the Hudson.
Deriving its name from the medieval cloisters that form the core of the building, it presents a harmonious and evocative setting for more than 2,000 exceptional artworks and architectural elements from the medieval West.