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Stranger Than Fiction
This has been a go-to date movie of mine since it's been out. Will Ferrell's life is being written for him, and he can only hope for a happy ending.
Why guys like it: Will Ferrell's awkward antics.
Why girls like it: Will Ferrell's awkward charm. 
Why you'll both like it: It's an original idea, but the story isn't bulletproof. In fact, I think there are several loose ends that are never resolved, but you'll get the gist of it even if you only watch it half the time—a perfect make-out flick.
 
Far And Away
I remember seeing Far And Away in the theater and thinking it was the most epic thing I had ever seen. It hasn't stood the test of time very well, but I still think it's a great romance story.
Why guys like it: All of those gritty bare-knuckle boxing scenes and plenty of trans-American adventure.
Why girls like it: A young Tom Cruise shows his butt for like, a second.
Why you'll both like it: An actual couple at the time, Kidman and Cruise have a tangible chemistry.

High Fidelity
High Fidelity gives hope to guys everywhere who keep screwing things up. It makes a good point, too; good taste in music won't help you with the ladies, nor will any other superficial posturing. It's good for guys to be reminded of this—I know I need to hear it once and a while.
Why guys like it: Cusack is the kind of cooler-than-thou a*****e guys secretly admire. Also, the soundtrack is a music nerd's goldmine.
Why girls like it: It's hard not to be disarmed by Cusack's baby face. Plus, he grows up in the end.
Why you'll both like it: There is a cute, happy ending after grueling fights and fits of jealousy. Make your move as the credits are rolling to Stevie Wonder's "I Believe."