Wes invites his best friend Chris over for a night in after being dumped by Henry. They attempt to blow off some steam by prank calling strangers, but soon realize that may have been the worst idea ever.

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, who goes off on her own to start a career as a stand-up comedian.