Release Date:  May 2, 2008

Definitely falling into the “something borrowed” territory artistically, Made of Honor is basically the male-driven equivalent of 1997’s My Best Friend’s Wedding. But instead of Julia Roberts doing all the scheming, we’ve got Grey’s Anatomy’s “McDreamy” (a.k.a Patrick Dempsey) as the single guy who doesn’t realize what he’s got until it’s (almost) gone.

From the opening scene, it’s quickly established how Tom (Dempsey) seems to have it all. Not only has his invention of the coffee sleeve made him fabulously rich, but he’s got an unlimited supply of gorgeous girls willing to follow all his rules (like no back-to-backs, meaning he won’t have sex with the same girl two nights in a row or invitations to family gatherings because it’ll give them the wrong idea—how considerate!) so he never has to wake up alone. And if that wasn’t enough of a dream scenario for a good-looking guy with questionable morals, he gets an enjoyable glimmer of domesticity each Sunday when he hangs out with his best friend, Hannah (Michelle Monaghan).

While we’re never quite sure why Hannah actually tolerates Tom (must be that McDreamy charm, right?), they have their comfortable rituals (like strolling through Central Park or eating dessert off each other’s plate) to remind viewers how they’re truly meant for each other. And while it’s pretty clear that Hannah would like Tom to just admit he loves her already, Tom’s pretty happy with the arrangement. After all, he’s got the best of both worlds, right? The doting best friend and all the bimbos he wants at his disposal.

With a father who is about to get married for the sixth time (and divorces again not long after) and a bunch of basketball buddies who don’t understand how casual sex without commitment is a problem, Tom doesn’t see a reason to take any of his relationships to the next level. Besides, the lone married guy in his group of friends isn’t exactly a glowing endorsement for matrimony—given the short leash he says he's on, thanks to his wife.

Of course when Hannah heads to Scotland for six weeks on business, Tom’s mindset shifts. When he immediately begins to miss her, he decides that he’s going to take the leap and pursue a relationship with her as soon as she gets back. But his plan ends up being too little, too late (shocker!) when Hannah unexpectedly meets a strapping Scot named Colin (Kevin McKidd), who ends up proposing before she heads back to the States.