Molly Mahoney is going home for her mother's wedding, and is bringing her boyfriend Lance to meet her family. Knowing they will be skeptical of him if she tells them he's in a band, she doesn't tell them anything about him, including his name. En route to the airport she discovers he's married and breaks up with him. At the airport, Molly meets up with Josh Shiffman, her brother's playboy best friend from childhood, as he is also flying from LA to Chicago for the wedding.