Peter and Bobby Farrelly hit their stride in the mid-to-late '90s with the one-two punch of Kingpin and There's Something About Mary, and that's really about it. They became the go-to guys for ribald, classless, and gross comedy, but since then, they've been out-done by so many other envelope-pushing comedies that their newest movie The Heartbreak Kid feels old hat. The Farrelly brothers seem to have run out of ideas for their big gags; in the third act, you can sense them straining to bring out the big guns while only packing a pellet gun. That's not to say the movie isn't funny. There's some of the better raunchy, gag-less comedy material they've done in the opening and middle acts, but there's a point when the script becomes bogged down by a completely convoluted, typically romantic-comedy misunderstanding. Instead of having a hopeless schmuck caught in inappropriate situations, the script by the Farrellys, Scott Armstrong, Leslie Dixon, and Kevin Barnett (a remake of the 1972 film of the same title based on a short story by Bruce Jay Friedman) decides to turn the schmuck into the reason for the inappropriate situations, and the strain of accepting the whole thing gets considerably tougher.

Eddie Cantrow (Ben Stiller) is a lifelong bachelor. The closest he's ever gotten to marriage is an engagement to a woman he dated for five years, but he broke it off, in part because she didn't like Caddyshack because the gopher looks fake. His father Doc (Jerry Stiller) is worried about him, not necessarily because he's not married but because he's not getting any action (Doc has a lewder phrase for it). Eddie attends ex-fiancée's wedding, and his married buddy Mac (a consistently funny Rob Corddry in a clichéd role) tries to convince him of the joys of marriage and points him out when the bride and her father make jokes at his expense. Soon after, he's walking down the street, watching the happy couples dining together, when he witnesses a man stealing a woman's purse. He tries to stop the mugger and gets a face full of perfume as reward. The woman is Lila (Malin Akerman), and Eddie can't bring himself to ask her out, an inaction upon which Doc and Mac harp. Lila shows up at Eddie's sporting goods store, though, and he takes her out. Their relationship progresses (in a make-out montage), and when she is called away out of country for her job, he finally takes the plunge.

Lila seems sweet and innocent, but once the happy couple is on their way to Cabo for a three-week honeymoon, things change pretty quickly.