Matt and I are lucky enough to have strange and eclectic tastes that mostly overlap. We can happily watch everything from Diehard to Hairspray together without owing each other any favors, but in honor of Valentine's Day, this February list shall be a tribute to date movies that dare to cross and blur the gender barrier within a single story. All of them offer at least a little good romance, an uninsulting showing for both its female and male characters, and (as if that weren't enough for any viewer with a soul), at least a little stereotypical entertainment for the guys.
So instead of going out to a certain theatrical release softcore porno based on a fanfic which equates sexual adventurousness with wildly emotionally abusive relationships, stay in with...
A Fish Called Wanda is an awesome collision of English and American comedy, expected tropes and insanity.
Wanda (a human played by Jamie Lee Curtis, after whom another character named his favorite pet fish), is one of a team of jewel thieves trying to cheat each other out of their take.
Archie turns out to be not only nicer but much smarter than Wanda's usual marks, a mental match for her (unlike Otto), and eventually begins to catch on to what's going on, but not before they can form a more real connection than she intended. It's fun and sweet, but we get there through a gauntlet of double-cross drama and Otto-lunacy which devolves into a live action cartoon by the end.
If this scene alone doesn't get a giggle out of both you and your date, I don't know what will.