Luke McKnight is an out of work actor looking for his next gig and dreaming about his old college roommate Andy Jones. After a drunken one night stand, they went their separate ways but Luke has never forgotten.

Andy Jones is a struggling artist with only one goal. To gain access to his trust fund. But the only way for him to do that is to get married. So Andy and Luke concoct a plan to get engaged, marry, and split the fund between them. But as Andy's family help plan the big day, everyone gets wrapped up in marriage plans, including Andy and Luke.

But Andy's sister Alyssa grows to hate Luke on sight and is determined to stop the wedding at all cost, and she's not afraid to pull out all the stops. Including making Luke's life a living hell, and invoking the anger of the one person that Luke loves and fears in equal measure, his daddy bear Caleb Olivera.