As Tom, a wealthy New York ladies' man who goes shirtless every other scene, Dempsey struggles uphill against a fundamental flaw in the script: His character's a jerk. Having made millions right out of college by inventing coffee-cup collars, Tom has nothing to do all day but pick up models in Starbucks and play basketball with his testosterone-addled buddies (Kadeem Hardison plays the married, whipped, "sensitive" one).
Saving Tom from withering up and blowing away entirely is his longstanding friendship with Hannah (Michelle Monaghan), an art restorer and the movie's idea of a sensible Plain Jane. To put this over, the lovely Monaghan ("Kiss Kiss Bang Bang") has been lit and filmed as unattractively as possible. In some states, this would be considered a felony.
The two share Sundays and secrets together - they're a couple, only they don't know it. When Hannah travels to Scotland for six weeks, Tom misses her so badly he decides he must love her; to his dismay, she returns with a fiance, a hulking slab of Mr. Perfect named Colin (Kevin McKidd in the old Ralph Bellamy role). If Tom's a prince of the city, Colin's a duke. Of Scotland. With four castles - one for each season.
Once Hannah asks Tom to be her maid of honor, director Paul Weiland stops at every appointed comedy station: the dress fitting, the bridal shower, the lingerie shop. If you've seen the trailer, for all intents and purposes you've seen the movie. The name of the production company is Original Film, which in other circumstances - those in which Sara Bareilles's "Love Song" didn't play over the opening credits - would be hilarious.
Dempsey does give Tom interesting little fits of frustration as he tries to sabotage the nuptials and still be the best male maid of honor ever, and "Made of Honor" might let loose if he decided to go for all-out warfare or if he really delved into his feminine side. The movie's ultimately as passive-aggressive as its hero, though.
And after a while you start to notice the script's curious mean streak: the pathetic nerd (Kevin Sussman) who keeps horning in on the boys' basketball game; Tom's clammy-handed Internet stalker (Christine Barger); the bridesmaids who could be named Dumpy (Emily Nelson), Skinny (Whitney Cummings), and Psycho (Busy Philipps). Even the usually classy Sydney Pollack gives off crass fumes as Tom's much-married father. In "Made of Honor," the leads are beautiful and everyone else is a freak. So where does that leave us?