In the premiere episode, "Pilot," it's New Year's Eve in New York. Trevor has changed the ball drop sign in Times Square from "Happy New Year" to "Holly I'm Here" for a lovelorn street musician who hopes his message will reach his intended. Despite his good intentions, though, the antics and persistence of Trevor -- who may or may not be a god -- land him in a mental institution for three months. Eventually he's found to be harmless to himself and others and is released, but under certain conditions. Placed under the care of Dr. Claire McCrae, he must attend her singles group therapy sessions on a regular basis so that she can monitor his progress. As it happens, Claire's singles sessions are an ideal place for Trevor to aim his Cupid arrows, so he's more than happy to accept this provision.

Trevor wastes no time in going about Cupid's business. He focuses his matchmaking efforts on Dave, the talented street musician from New Year's Eve, to find the woman Dave had a brief encounter with at a pub in Dublin. Anxious to match his first couple, Trevor arranges for a reporter named Madelyn to do a story on Dave's search, but Claire, who believes that love at first sight is a myth, doesn't hold out much hope for a happy ending.

Meanwhile, in need of a base from which to fulfill his mission of bringing together romantically challenged couples, Trevor rents a room above the struggling Tres Equis Cantina owned by Felix Arroyo and his sister. In exchange for rent, he becomes a bartender and creates an atmosphere for singles looking for lasting love.

Could Trevor Pierce really be Cupid? No one believes his story, but everyone finds him quite charming and, after all, he does possess a great knowledge of mythology. Despite their differing views on romantic love, Trevor knows he can turn to Claire for help and friendship. Only time will reveal who will win the battle for love.

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.