Robert, a middle-aged gay man, begins a personal documentary project following his long history of failed relationships. As a professional but emotionally vulnerable individual, Robert decides to interview six of his ex-boyfriends, each of whom represents a distinct chapter in his love life. His ultimate goal is to find out why these relationships ended and to use the documentary as a means of personal growth—or so he believes. With the support of his sister Deborah, Robert prepares for the emotionally challenging task ahead.

Sabrina, a successful divorced attorney must juggle her family and guests during Christmas dinner when her daughter, Leslie, surprisingly brings home her new fiance, Juan, and also invites her father, Glen, Sabrina's ex-husband.