Loosely based on a true story, "The Gambler" is a romantic comedy about how Emma (Hudson) helps writer Alex (Wilson), whose jam is that he has writer's block and his gambling debts have put him in trouble with loan sharks. To get them off his back, he must finish his novel in 30 days, or they'll kill him. What will intrigue the viewer is how two very different people share a potentially deadly situation creatively and co-operatively.

Trying to help him complete his manuscript is stenographer Emma. When Alex dictates his tale of a romantic love triangle to the charming yet opinionated typist, Emma challenges his ideas at every turn. Her unsolicited input is intriguing, and begins to influence Alex. Soon, his story real life inadvertently begin to imitate art.