Luke and Kate are coworkers at a brewery who spend their nights drinking and flirting heavily. One weekend away together with their significant others proves who really belongs together and who doesn't.

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.

Coming-of-age story about a suave 15-year-old prep school student who falls in love with his stepmother. When her best friend responds to his advances, he suddenly finds himself in way over his head.

The Great New Wonderful weaves five stories against the backdrop of an anxious and uncertain post-9-11 New York City.