Successful Hollywood agent Bryce Dixon is returning to Alabama for the first time in 15 years for his high school reunion. When he learns he's the only one of his friends who isn't married with children, he convinces his client, starlet Madison Belle, to pretend to be his girlfriend. But he soon learns that success has different meanings, and romance may be closer than he thinks.

Bryce is ready to propose to Madison while they visit her family for Christmas. However, the spontaneous wedding of Madison's sister Harper throws Bryce's perfect proposal plans into a tailspin.