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.
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.
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 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.
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.