The Little Mermaid
Guys: This one may get you laid, but it could also convince your date that you’d love three daughters (or more!), you’ll totally help wallpaper their bedroom in floor-to-ceiling Disney regalia, host Jasmine-and-Cinderella-themed birthday parties and take them trick-or-treating. In other words, you’d better really like the girl before you spring for tickets on this one.
Ladies: There’s nothing I’d rather see with an XX chrome. He may go with you because he’s afraid you’ll punish him if he doesn’t, but he won’t enjoy it, no matter how metro he is. If he gets tickets, realize that a Bugaboo Frog stroller is just around the corner. Bottom line? Take your niece.

Mamma Mia! and Xanadu
Guys: I don’t care if you just smashed the pedicab driver in the face—your mate will question your sexuality if you take her to either of these shows. In Xanadu, the main character gyrates in roller skates and skintight denim cutoffs. In Mamma Mia!, the male leads dance about in tiny wetsuits while singing ABBA.
Ladies: You know how some couples have a quid-pro-quo movie trading system? Like, for every period drama starring Keira Knightley you make him endure, you’ll have to suffer through a bloody Coen brothers film? Under that system, if you drag your boyfriend or (God forbid) first date to one of these, you will have to watch war movies for the rest of the year as penance. Pass.

Rent
Guys: Want to be her hero? Take her to this modern update of the opera La Bohème before it ends its run in September. It doesn’t matter if she’s gone once or 14 times in every city it toured since she was 16. In the unpredictable world of dating, these tickets are the closest you can get to a sure thing. It’s the fastest, cheapest, easiest way to be seen as sensitive, intelligent, thoughtful, deep and sweet. You cannot lose.
Ladies: Who cares if he doesn’t understand why you cry every single time you see Angel die. It might be a bit much for a first date, but if he can’t handle this, he’s not the kind of man you want to date anyway.

Spring Awakening
Guys: It won the Tony for Best Musical, so you think you’re safe…but you’re not. It can very easily be the most awkward two hours you’ll ever experience, or a way to bring your burgeoning relationship to a whole new level of intimacy. You’d better understand what kind of girl you’re really dealing with before you sit down to this one, because once you watch simulated, date-rapey sex onstage, there’s really no going back.
Ladies: This musical includes abortion, suicide, incest and masturbation. Guys will love it! Unless they’re uptight bankers, in which case they’ll love it (but later that night, they’ll secretly want to be alone with their Craigslist Casual Encounters)! Either way, you’ll probably be seen as a badass for taking them to anything that involves groping a 19-year-old onstage. Just don’t be surprised when they grope you trying to get into the spirit of things.

Wicked
Guys: This is a toughie. Most women love the fabulous music and beyond-belief singing. But it might be better if you bought her tickets and told her to go with her best girlfriend. Then again, you may enjoy the creatively told backstory of Oz. And there are flying monkeys.
Ladies: Buy tickets (it’s amazing), but not for him, unless (A) you’ve been dating for months. (B) he quotes Lindsay Lohan’s teen flick Mean Girls, or (C) he loves watching the CW’s guilty pleasure Gossip Girl with you and it’s not because he fantasizes about a threesome with Blair and Serena. But if you are dating a guy like that, could you please set me up with his brother?

So there you go, theater buffs. Ticketmaster awaits.

E-mail her at julia@timeoutny.com.

See previous Julia Allison on dating