Andy (Adam Scott) has just lost his job and is forced to move back to his hometown in New Jersey. While home he decides to look up his old high school ex girlfriend Kim (Ellie Kemper) who he broke up with on prom night for a more popular girl. She doesn’t seem to want anything to do with him. Then while out with his old best friend Sam (Jason Sudeikis) who has become a smarmy womanizer who loves seducing woman with low self esteem he convinces him that Kim should have been the one. Andy leaves Kim a drunken voicemail confessing his love and apologizing for making the biggest mistake of his life.
While recovering from his hangover and walking home from Sam’s someone dressed all in black runs out of a jewelery store carrying a bag of stolen merchandise and runs into him. They drop the bag and run off and Andy is left there holding the bag. The police come and don’t believe him and they arrest him for the robbery!
Andy is about to be sentenced when Kim shows up in court and offers to take custody of him. The judge releases him to her supervision saying if he doesn’t follow her upstanding lead he’ll be back in jail. Once in the car Kim reveals that she is the robber and turns on the crazy blaming Andy for turning her to a life of crime when he left her. But now she owns him and he has to make it up to her by becoming her partner, in crime AND MARRIAGE!
Andy becomes a nervous wreck and they become a bumbling Bonnie and Clyde. Andy’s probation officer, Officer Jamie has been taking a shine to him (played by Kristen Wiig). She knows what’s going on but won’t arrest him and just wants him to come clean to her but out of fear for the increasingly psychopathic Kim he won’t.
As the biggest heist Kim plans their wedding for town hall while gold bars are getting moved through there. During their vows while looking at Officer Jamie he confesses the whole thing. Both of them get arrested and we see at the end Andy and Jamie having a budding romance through the glass of a prison visiting room.