Weekend trips, office parties, late night conversations, drinking on the job, marriage pressure, biological clocks, holding eye contact a second too long… you know what makes the line between “friends” and “more than friends” really blurry? Beer.

Beautiful, sophisticated women are all over Oscar Grubman. He is sensitive and compassionate, speaks French fluently, is passionate about Voltaire, and thinks the feature that tells the most about a woman is her hands. On the train home from Chauncey Academy for the Thanksgiving weekend, Oscar confides in his best friend that he has plans for this vacation--he will win the heart of his true love. But there is one major problem--Oscar's true love is his stepmother Eve.

On the way to meet with an independent artist in the South, newlywed art dealer Madeleine is convinced by her husband, George, that they should stop to meet his family in North Carolina. Madeleine's affluent lifestyle clashes with the family, but she befriends George's wide-eyed and pregnant sister-in-law, Ashley, who is nearing her due date. Through the family, Madeleine gains greater insight into George's character.

Tim and Lee are married with a young child. The chance to stay at a fancy home in the Hollywood Hills is complicated by Tim's discovery of a bone and a rusty old gun in the yard. Tim is excited by the idea of a mystery, but Lee doesn't want him to dig any further, preferring that he focus on the family taxes, which he promised to do weeks ago. This disagreement sends them on separate and unexpected adventures over the course of a weekend, as Tim and his friends seek clues to the mystery while Lee searches for answers to the bigger questions of marriage and parenthood.