Adam (Chris D'Elia) is a thirty something year-old man child who lives a ridiculous lifestyle with his three life-long friends. After a series of events such as getting evicted from the house they ruined together and his ex dating a super successful famous guy, Adam decides it's time to grow up by "breaking up" with his friends.

Nate, a 19 year old film student, and Margaret, a 52 year old spinster, are best friends in an odd, quirky, totally working kind of way... until Nate's audacious classmate Darla sets him up on a date with James. Nate's new life shakes apart his friendship with Margaret, just as she is trying to start a career as a stand-up comedian.