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 makes a mistake and questions past relationships when she and AJ attend an ex's wedding.

Ruby thinks her new client, Isaac, is a stalker and must warn her exes that they may be in danger.

After Richie confronts her, Ruby muses about her past and finds a loophole in her exes' deaths.

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 reconnects with the “one who got away"; AJ makes a crucial discovery in the case.