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?
New York's new resident, Cupid, must orchestrate 100 happily-ever-afters before he is allowed to return home to Mount Olympus, punishment from the Gods for the current sorry state of love. Sent without his trademark bow and arrow, Cupid must learn what really makes love work as he navigates the modern metropolis of New York City.
There, living under the name of Trevor Hale, meets famous psychologist and author Dr. Claire Allen who too is dedicated to helping lonely souls find happiness though she has a very different view on love than Trevor. As they work together, Claire tries to figure out who Trevor really is. Is he Cupid, or just a man who has lost his mind?