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 believes the recent deaths are the work of a stalker and suspects her new client, Isaac; AJ insists Ruby must track down all her exes to warn them they're in danger, forcing her to confront how she's treated people in the past.

After Ruby's ex, Richie, confronts her about the sex timeline and his imminent death, she continues looking inward; after warning one celebrity on her timeline, she discovers a loophole in the pattern of her exes dying.

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', who gives her more insight into how she is in relationships; AJ makes a discovery that changes the course of the case.