When Ruby learns a guy she briefly dated in college has died, she attends his funeral to make up for how selfishly she treated him; this sets her off on a path of examining her past choices to move forward with her present love life.

Ruby attends in-person therapy for the first time in years; when her therapist suggests she take a break from romance, it proves to be more of a challenge than anticipated.

Ruby must decide who she loves the most while also learning some news that points the case in a whole new direction.