A psychologist, Dr Claire Allen, is ready to abandon her plans for her latest book on love and romance when a colleague introduces her to an institutionalised patient claiming to be Cupid. After a weeks of therapy sessions, the man "remembers" his "real" name: Trevor Hale. Believing that he is cured, the state mental health board agrees to release Trevor's on the condition that Claire continue to monitor his progress.
Linguist Jennings Crawford is hired to teach elocution to a lower-class woman so that she can impress her upper-class fiance's family, but the teacher and student find that they have chemistry of their own.
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 whom she sees everyday on a billboard across the street from her work. Meanwhile, Champ is asked to do some modelling; reluctant, he finally decides to go for it when he realises how much this exposure can help his burgeoning career as an actor.
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 ...
With Halloween just around the corner, Trevor feels there is an opportunity to make Champ's dream come true to experience a one-night stand. He also invites Claire's other patients to the party, telling them to forget their inhibitions and to just have fun.
A new guy in the singles group introduces Trevor to an alternative and aggressive method of dating, which just might be his ticket back to Mt. Olympus. However, Helen has put Trevor's libido to the test. if he gives in, he could be stuck on Earth forever.
Trevor tries to match two strangers despite one's terminal illness and destiny delivers a magical twist-of-fat. Claire and Alex have growing pains as the next step in their relationship becomes more of a hurdle.
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; Claire revisits an old nemesis in hopes of discovering clues to Trevor's true identity.