Milo Boyd (Butler) is a former New York Police Department detective who works as a bail enforcement agent (bounty hunter). Milo's ex-wife, Nicole Hurley (Aniston), is an investigative reporter. When Nicole receives a tip on a story, an apparent suicide that may have been a murder, she skips her bond hearing (after been arrested for assaulting a police officer) to meet her informant, causing the judge to revoke her bail and issue a warrant for her arrest. Milo is ecstatic when Nicole's bail bondsman, Sid (Jeff Garlin) offers him the job of bringing her to jail, for a bounty of $5,000. Milo apprehends her at a race track in New Jersey, and is not interested in explanations until Nicole admits that she's found evidence that implicates their mutual friend and Milo's ex-partner on the police force is involved in the story she was following, and Milo decides to investigate with her.
This film contains examples of:
- Bounty Hunter: Well, duh; Milo is a bounty hunter.
- Ooh, Me Accent's Slipping: Gerard Butler plays an American, but his Scottish accent slipped through a lot from time to time. Notably, the trailer has him utter the line "duly noted" in a manner where one can slightly detect it.
- Crocodile Tears: Nicole tries this on Milo to get him to release her from the trunk. It doesn't work.
- Felony Misdemeanor: Invoked regarding Nicole's arrest; she apparently assaulted a police officer, but what she really did was graze a police horse (without causing it serious injury) while trying to find a parking space; it's just unfortunate for her that the horse counts as a police officer rather than just a means of transport.
- Punk in the Trunk: When Milo apprehends Nicole at the race track in New Jersey, he throws her into his car trunk and drives back towards Manhattan.
- Red Herring: Nicole uncovers evidence incriminating Bobby, Milo's best friend and the man who walked Nicole down the aisle at their wedding, as part of the conspiracy; it turns out he was just forced to take part.
- Rom Com Job: Of the "Creative Media Jobs: Print" variety; Nicole works as a reporter for a newspaper.
- Spotting the Thread: Nicole initially becomes suspicious of the apparent "suicide" because the dead man would have allegedly jumped through trees and hit the ground head-first; if he was serious about killing himself the trees might have broken his fall (or at least slowed it to a non-fatal speed) when he would have gone straight to the pavement if he jumped off the other side, and anyone jumping off a building would hit the ground feet first.
- Stalker with a Crush: Stewart, Nicole's coworker, has a crush on her, and stalks her and Milo bent on rescuing her from Milo. Stewart ends up being confused with Milo by thugs sent by Irene, a bookie, because of Milo's outstanding gambling debts and kidnapped in his place.
- Working with the Ex: Milo decides to work together with his ex Nicole to help her with the story she was following.