As Cupid, Trevor thinks that the tribunals at Mt. Olympus might be right about his failing instincts, since he's been having little success in his matchmaking efforts. He tries again when he senses a potential match between Claire's friend, Riley, and Mick, a private investigator who took photos of her with a married man. The new relationship starts to go awry and Claire must walk the line between therapist and friend, as Riley has decided to try Trevor's method of jumping into love feet first. Meanwhile, as Felix plans his parents' 40th wedding anniversary party, he becomes smitten with the divorced mother of Lita's new boyfriend, causing strife between the siblings.