Chicago elementary-school nurse Emily is in Costa Rica as the maid of honor for her longtime best friend Phoebe, the imminent beach wedding to get away from Phoebe's mother Sue's preference of a stuffy country-club wedding back in Chicago. Phoebe and her fiancé Jamal have been Emily's emotional supports in the recent breakup with her ex-boyfriend Shane, whom Emily thought was the one. Emily being prone to mishaps follows her to Costa Rica, with Jamal's best friend/best man Ryan, who recently moved to Costa Rica from Chicago, always seeming to be the one to clean up the messes. Emily has always had an issue with Ryan; Phoebe and Jamal know this, just not her reasons. The latest mishap two days before the wedding has a monkey stealing Emily's backpack on a secluded beach. Emily implies that she is most desperate to find it because her phone is in it, which Phoebe and Jamal don't doubt, knowing that she's been cyberstalking Shane, trying to reunite with him. But Emily's really panicking because she left Phoebe and Jamal's irreplaceable wedding bands in the backpack. Only telling those on a need-to-know basis about the rings going missing, Emily goes on a quest through the jungles of Costa Rica to find her backpack and thus the rings, Ryan offering to accompany her, being the one who knows the country the best. In their quest, which if they are unsuccessful could well be the last straw and spell the end of Emily and Phoebe's friendship, Emily and Ryan get into one misadventure after another, but their confined time together might give them a different perspective on their relationship.