Brad (Ben Stiller) is having a mid life crisis due to his friends in college becoming more successful. His former college friends are Craig Fisher (Michael Sheen) is a successful tv personality after working in the white house, Jason Hatfield (Luke Wilson) is a successful hedge fund manager, Billy Wearsiter (Jemaine Clement) who retired at 40 after selling his tech company and is living in Hawaii, and Nick Pascale (Director Mike White in a Cameo) is a successful movie director. All Brad has to show for it that he runs a non profit.
Brad's son Troy (Austin Abrams) is a musical prodigy who could quite literally get into any college that he wants. Troy interviews both at Harvard and Tufts. Though Brad has to call Craig who he hasn't seen in ten years to help get Troy an interview after a mix up.
Brad eventually meets Craig for dinner. Where Brad learns from Craig that Nick is going bald and is having a increasingly decadent lifestyle, Billy is an alcoholic, and Jason lost a whole bunch of money for some high powered people and quite possibly is going to jail.
Brad eventually meets up with Troy at a concert where several of Troy's friend are playing. Afterwards Brad feels that he made the right choices but still has doubts.