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Le Docteur Claire McCrae fait la connaissance d'un patient très, très étrange qui prétend être...Cupidon ! Trévor Pierce, puis que c'est son vrai nom, va être très déstabilisé quand il va apprendre que Cupidon est... marié ! Cependant, le Dr McCrae va vite se rendre compte qu'elle n'est pas sorti d'affaire avec ce patient...

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.

Marshall, a sweet but bullied teenager, turns to Trevor to fix up his left-wing mom, Hallie, with his boxing instructor, Clint, the sperm donor who made Marshall's birth possible.

Claire's apartment is burglarized and she finds herself leaning on Trevor for support. Meanwhile, Trevor tries to match-up an ex-jewel thief with his parole officer.

Trevor is trying to convince Claire to make a Mardi Gras theme party for her singles group. At the same time Trevor wants to bring back together a couple of high-school sweethearts.

Trevor aims his Cupid love arrow toward Jack, a radio disc jockey with a love for classic rock n' roll, and one of his listeners, a single mom named Sarah. On the couple's first date, Jack and Trevor arrange a performance by Robert Harrison, the lead singer from the indie band Future Clouds and Radar. All is going well until Jack unintentionally disappoints Sarah's 13-year-old son, Adam; and Sarah discovers a secret about Jack. Also, Claire becomes smitten with a handsome statistician who is helping her create a test that matches people up based on their commonality - a concept she readily embraces.

A dialect expert is enlisted by Claire to seek clues to Trevor's origins, and by Trevor to act as Henry Higgins.