The carnival 'medium' Bella arranged for all girls at her sister Daphne Bloom's hen night convinces Bella she'll marry one of her exes within the year or die utterly lonely. Taking that seriously, she ignores her dependable ex Elliott Mayer, whom she only meets on account of shared custody of dog Rufus. Instead she tries to make up with hyper-emotive rock musician Johnny Diamont, whose heart she crushed a year ago by dumping him on his by-the-way-forgotten birthday. Johnny hesitates whether to take her back or exact just revenge.
Although finding ex Tommy's cat made belle volunteer to mind it, in the process she meets another ex, Jake Turner, whom she dumped after perfect months for 'stopping to make an effort' couch potato-style. He's now an editing executive and a physically stunning sports buff, so their dates prove bodily excruciating. Yet she ends up dumping Jake again on account of references to his other ex.
A burglar has robbed Bella. When she reports it, the police who arrives is Ronnie Helton, Bella's ex from 1991, her sophomore year. Bella's dad was not too fond of the "bad kid of the school", and does not like him 17 years later either. Bella, however, is very interested when she finds out that Ronnie is single.
When Cyrus convinces belle to come along and enjoy perfect surfing weather, they bump into her ex Shane Gallagher, whom she dumped for being an irresponsible beach bum, however hunky. Now he's a well-sponsored surfing star and still gorgeous, so she's interested again. Ironically, his obligations pose a problem, he now only plays the bad boy every woman swoons about. Augie finds the shower head he installed pleases his wife too much. Cyrus is after fringe benefits and a foxy girl who wants surfing lessons, but falls prey to Hawaian scam artist Mini Van.