The most fun and memorable nights I have in NYC seem to follow this pattern:
Meet friends - Chitchat, break bread, grab a pint, etc.
Attend Comedy Show - The less mainstream the better.
Socialize - Go for drinks, dancing, or another random suggestion from someone in group.
The linchpin is the Comedy Show since it always sets a great mood for the rest of the evening. Plus, who doesn't like laughing with friends, and checking out new shows?
With that in mind this group's mission is to check out good comedy shows, and create a fun social experience among friends (see formula above). Each event I will secure a set of tickets for a show (Stand-up, Improv, Sketch, etc.), and anyone is free to RSVP. If you can't make the comedy event feel to join for the socializing afterwards. Bring a friend or come alone, just be open to meeting someone new.