Entrepreneur Perry Tompkins feels like a town traitor. His crime? Leaving his small Virginia hometown to run a tech business in Silicon Valley. But this Christmas, the town's cold shoulder can't dampen Perry's holiday cheer. Because his longtime friend and secret crush, Sharmaine, has finally broken up with her boyfriend—the town's golden boy, Lance. And Perry's coming home for the holidays with a mission: Operation Win Sharmaine. Sharmaine Cole may not be with her ex, Lance, anymore, but she still wonders why he’s been acting so strangely. Suspecting that it may have something to do with his family’s store, a local historical landmark, she enlists her close friend Perry to help. Sharmaine may think that Perry is the perfect partner-in-crime, but the last thing he wants to do is bring her closer to her ex. But when the woman you love asks for help, and a local treasure is at risk, how can you say no?