Buy a GO NYC pass - this provides discounts and entry into lots of museums in NY. A lot of people (singles as well as couples) hang out at museums. The Metropolitan Museum of Art is incredibly busy on a Friday night. You can go by yourself and not feel weird about it at all. (I've done it lots of times.) The Museum of Natural History is nice too, and they have a wonderful cafeteria in the basement - its a good thing to do around lunchtime in the city. Grand Central Station is absolutely beautiful so you should check that out. There's also a food court downstairs, so you can get some cheap food. It's fun to walk around Soho - so many shops to check out (even just window shopping) - There are lots of little cafes in Soho as well, many of them offer Sat. and Sun. brunch for a really good price.
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