Chance Hazelton owns a struggling, "hard-to-find" gift shop called "Gifts by Chance." As the Christmas shopping season approaches, Chance is hired by William Richards, a wealthy and popular entrepreneur to help him organize the perfect proposal for his girlfriend Leyla Brooks. When Chance needs to get closer to Leyla to find out what she likes, they devise a plan to have her attend their Christmas party as an old friend of the family. Chance and William continue to spend more time together with the hopes of devising the perfect proposal, but Leyla does not seem to be ready for marriage and each plan seems to fall apart. As Chance and William get to know each other more they begin to bring out the best in one another. Chance begins to see that there's more to life than living in the past and William starts to find out who he is beyond his public image.