Although Brad has a satisfying career, a sweet wife and a comfortable life in suburban Sacramento, things aren't quite what he imagined during his college glory days. When he accompanies his musical prodigy son on a university tour, he can't help comparing his life with those of his four best college friends who seemingly have more wealthy and glamorous lives. But when circumstances force him to reconnect with his former friends, Brad begins to question whether he has really failed or if their lives are actually more flawed than they appear.

Mike and Dave are young, adventurous, fun-loving brothers who tend to get out of control at family gatherings. When their sister Jeanie reveals her Hawaiian wedding plans, the rest of the Stangles insist that the brothers bring respectable dates. After placing an ad on Craigslist, the siblings decide to pick Tatiana and Alice, two charming and seemingly normal women. Once they arrive on the island, however, Mike and Dave realize that their companions are ready to get wild and party.