Would you recommend the Madison Square neighborhood in New York City for singles?

Eh, no. Most of the singles area is downtown. Anything above 23rd is pretty limited as far as the nightlife scene goes. And, Madison Square is in a bizarre spot seeing as it's nestled next to the sleepy Gramercy and commercial Flatiron and Midtown. There aren't really any bars in the area and the restaurants are high end and sparse.