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When a man claims to be Cupid, he is placed in the care of a psychiatrist who takes him under her wing. Obsessed with his mission on Earth, the man now known as Trevor Hale decides to help a woman find her true love.

Still intrigued with Trevor, wondering who he really is and where he comes from, Claire jumps on the opportunity when she meets a linguist who seems able to tell someone's origins just from his patterns of speech. She introduces him to Trevor, who - of course - cannot resist helping the man when he learns that he is still a virgin.

A woman seeks Claire's help when she fears her marriage is in jeopardy because her husband feels frequent and sudden urges to sing and dance in public.

Claire is receiving strange gifts from a secret admirer. While she slowly begins to fall for him, Trevor helps one of her patients meet the man of her dreams - a man she sees everyday on a billboard across the street from her work! In the meantime, Champ is asked to do some modelling ; reluctant, he finally decides to go for it when he realizes how much this exposure can help his burgeoning career as an actor. Structured like a fairy tale (""once upon a time, there was a princess...""), this episode is a wonderful example of television at its best. Also, Trevor's feelings for Claire become quite obvious with this episode.

Champ introduces Claire and Trevor to his long-time friend Sophie, a would-be singer who just signed a contract with a record company. When Sophie claims she does not believe in love, Trevor feels obliged to prove her wrong. They start discussing the past and Sophie's one-time crush, when she was a kid, comes to the surface. They decide to go back to her hometown and see what her old love interest has become, hoping that maybe something magical will happen. Claire is concerned and quite against the whole idea until her superior says that Trevor may have to be committed to a mental institute. She then feels that this little adventure may help her further her knowledge of Trevor and help decide on what to do with him... This episode contains a number of black & white flashbacks, offering scenes of Sophie's, Champ's and Claire's youth. Obviously, Trevor was left out of the loop...

Champ tells Trevor that everytime he meets a girl, he ends up in a relationship. For once, he would like to experiment a one-night stand, to know how it feels. With Halloween just around the corner, Trevor feels this is the perfect opportunity to make his friend's dream come true. He also invites Claire's other patients to the party, telling them to forget their inhibitions and to just have fun. As for Claire, he challenges her, certain that she would turn down any man even if he were perfect for her. To prove his point, he searches and finds Alex, who seems a perfect match. While Claire first does seem reluctant, she finally falls under the man's charm - much to Trevor's dismay.

Trevor is growing desperate. Caught between his desire to return home and his jealousy at seeing Claire having a serious relationship with Alex, he makes his first mistakes as a love counselor. On one side, he encourages a man to use a ""sure score"" pick-up technique that gets him the woman he wants but leaves him distressed and disgusted with himself for he feels he cannot be with a woman that would fall for such a trick. On the other end of the tunnel, his friend and roommate Champ is starting a new relationship and Trevor can't help but intervene - and in ways that pushes the woman away rather than bring her closer. And somewhere in the middle, Trevor himself is caught up in a strange relationship with Helen Davis, a woman he met at the bar. They're both attracted to each other, but Trevor tells Champ he can't have a relationship with a mortal, or he'll lose his immortality. And yet, he might just be desperate enough to not want it anymore...

While looking for good romance videos to rent, Trevor meets Dan, the coach of a local hockey team. He invites him to a party at the bar, deciding that he should help him find his true love - namely, his neighbor Susan, a woman who seems to keep to herself, avoiding conversation and all contact with other people. Meanwhile, Claire is wondering why Alex seems to be avoiding her and fears that he may want to dump her. But the truth is that he is falling in love with her and afraid of his own feelings for her. Trevor finally manages to draw Susan to the party and have her meet Dan. But when she realizes that the man is trying to set her up, she flees. She later explains to Trevor that she cannot start a relationship because she only has six months left to live.

Claire is delighted when her old professor, Dr. Wyatt, shows up at her office. She announces that she has just published a book and Claire invites her to attend her next singles group. But when her mentor speaks up at the meeting, she is startled to hear her claim that love is a myth. Needless to say, Trevor is just as baffled and, for once, the two of them are in agreement. Then Alex tells Claire that he was offered an important job - but in another city. Claire starts to doubt and lose her faith in the power of love...

While Christmas shopping, Claire and Trevor get caught up in jury duty. Claire has plans to spend the holidays with Alex and so - like most of the other jurors - would like to get this over with as quickly as possible. But Trevor, who was going to spend Christmas alone anyway, spots two possible matches and voluntarily votes differently then the others. He then desperately tries to convince everyone that the man who is being judged actually is innocent...

Trevor tries to help a new member of the singles group, a woman who wants to be loved for her personality rather than her looks, while Claire revisits an old nemesis in hopes of discovering clues to Trevor's true identity.

Trevor tries to arrange a match between a man who thinks he's Don Quixote and an exotic dancer, while Claire has a reunion with her jazz-musician father.

Trevor ruins a bachelorette party Claire is giving for her best friend when he reveals that her fiance has been having a long-term affair with a promiscuous former classmate.

Precocious twins ask Trevor to find a match for their single, down-on-men mom, triggering Champ's memories of a former relationship.