When record store owner and compulsive list-compiler Rob Gordon gets dumped by his long-time girlfriend, Laura, because he hasn't changed since they met, he revisits his top five breakups of all time in order to figure out what went wrong. As he examines his failed attempts at romance and happiness, the process finds him being dragged, kicking and screaming, into adulthood.

Upon hearing his wife was killed in the Iraq war, a father takes his two daughters on a road trip, all the while searching for the right time and place to tell them about their mother's fate.