7. Pretty In Pink (1986)
Chicks love this throwback Molly Ringwald flick, and even give bonus points to the man that's willing to grin and bear his way through John Hughes' 1986 rom-com about poor girl-rich guy love, but we'd proceed with caution.
Despite the happy ending for Andie Walsh (Ringwald) and her trust fund Romeo, more often than not, the first thing you'll hear girls talk about post-flick is poor Duckie (Jon Cryer), the protagonist's best friend who's hopelessly in love with her and ends up all by his lonesome. Roll credits. (Fortunately for Jon Cryer, despite his failure to bag the girl, there's no doubt that he's bagging more cash than any of his MIA co-stars with his high-paying role on Two And A Half Men.)
Next thing you know, though, your girl is looking at all of her friend zone dudes in a whole new light. And you can't have that.