Second chances and new beginnings. After the death of his wife, Geoffrey has resigned himself to a life of unfulfilling dates. Since the loss of her mother, Tessa no longer believes in the magic of Christmas. Enter Valentina del Torre. The matchmaker sees a spark between the billionaire and upcoming artist, she makes it her mission to bring them together. What Valentina doesn’t know is that the cupid arrow she launches will boomerang. While trying to help Tessa’s father, Sal, find a match of his own, Valentina realizes she’s falling for the man that she shared a childhood with in Rome. At the same time, Geoffrey and Tessa are facing difficulties in their fledgling relationship. With his two young children acting out, Geoffrey wonders if getting into a relationship with Tessa is the cause of their negative behavior. Can Valentina help them find their happily ever after? And will the matchmaker get a happy ending of her own?