Trevor Hale is Cupid. He was sent from Mt. Olympus to help 100 couples get together. In this pilot episode Trevor is trying to help Dave find his dream girl, without his bow and arrow, but he does have the help of his psychologist Dr. Claire Allen who isn't sure if Trevor is for real or not.

Felix makes arrangements to do a party for his parents 40th wedding anniversary. Meanwhile Trevor feels there is a match between Claire's friend and a private investigator.

A teenager ask Trevor to match his mother with his boxing instructor. Meanwhile Claire's mom moves in with her after a breakup with her boyfriend.

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 helps Jack, a radio disc jockey find love with a single mother that listens to his show. Meanwhile, Claire seems to be falling in love with a statistician.

In a riff on George Bernard Shaw's Pygmalion (the original play upon which the musical My Fair Lady was based), Trevor sets out to retrain a "lower class" massage therapist to make her more acceptable for the family of her "upper class" ex-boyfriend by connecting her with a dialogue coach to disguise her history. Also, Claire thinks she's onto a clue to Trevor's actual past, but is it a faux lead?