When 40-year-old San Francisco bachelor Eddie Cantrow (Ben Stiller) attends the wedding of his ex-fiancée -- and is seated at a "singles table" full of children -- he realizes maybe he's been too picky in his love life, and it's time to settle down. Fortunately, he doesn't have to compromise his standards when he meets Lila (Malin Akerman), a funny, attractive blond who does environmental research for a living. Lila's company wants to relocate her to Europe, but only because she's single -- they don't force married couples to uproot themselves. So Eddie hastily proposes to her, even though they've only been dating for six weeks. But the moment they exchange vows, Eddie starts to notice Lila's rough edges and annoying habits, which had remained hidden underneath her perfect exterior. Their Cabo San Lucas honeymoon gets off to a rough start full of tuneless pop singalongs and surprising revelations about Lila's job and her past. Things only get worse for a confused Eddie when he meets Miranda (Michelle Monaghan), a Midwesterner in Cabo for a family reunion -- and starts to wish he'd held out just a little bit longer. The Heartbreak Kid is Peter and Bobby Farrelly's remake of the 1972 Elaine May comedy of the same name, starring Charles Grodin.
by Derek Armstrong synopsis