Skip concerts. That's more of a second or third date thing. Concerts aren't really conversation-friendly. You can talk before the show, but it might be loud and crowded. Plus, there are too many variables that could potentially make for an awkward time. What if the band goes on late? What if the opening act sucks? Then you're stuck listening to a terrible band and have to shout over music if you want to talk. What if the band you're seeing has an off night? What if the crowd is rowdy? True story: A friend of mine was once on a first date at a concert where a riot broke out. It made for a good story after the fact, but a terrible first date.

So think about fun activities that will allow you to get to know each other. Check out your local free weekly for bars with trivia nights, video games, board games, skeeball, or offbeat themes. (Tiki, old-fashioned speakeasy, Heathers-theme, classic arcade games, ping pong, speakeasy that also sells hot dogs...NYC is full of theme bars, and the trend is spreading.) Drinking while playing a game is catnip to hipster geeks. So is laser tag and mini-golf.

Or maybe grab a bite to eat or coffee at a trendy cafe and then browse a vintage clothing store, comic book shop, or indie music store. That way you'll get to know his interests, and be able to chat.

If you still want a live event to take him to, opt for comedy over music. Avoid the two-drink minimum at the Chuckle Hut and take him to see an improv comedy or a show featuring up-and-coming comedians. (If Patton Oswalt, Louis CK, Demetri Martin, and Aziz Ansari are in town, those are safe hipster-friendly bets.)  

Finally, don't worry too much about impressing him. Focus on getting to know him. If he likes you, he'll have fun doing whatever you suggest. Any guy who would scoff at your first date idea belongs on Look at This F*ing Hipster, not in your heart.