Glendon Palmer

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.

After a high-profile firing, everything is at stake for 40-year-old Jenna: her career, her ticking biological clock, and her bank account. Her fashion career comeback hits a snag when she falls for a charming, much younger coworker — who happens to be her boss’s son. As sparks fly, Jenna must decide if she’ll risk it all on a secret romance with the one person who could destroy her comeback.

Two very different families converge on Martha's Vineyard one weekend for a wedding.