William Holt is the heir-apparent to the top job at Chicago-based Holt Enterprises upon his father Jim Holt’s imminent retirement. Will has coasted through life on his charm leaving others—such as his unofficial assistant Lyle—to clean up his messes. Reluctant to leave the company in Will’s hands, Jim posts a position for a lawyer to shadow him and handle any messes of a legal nature. This is how Will meets lawyer Annie Park, who specializes in family law. While Will believes she came to the Holt building for the job, she actually came to confront him about Holt Enterprises tearing down the building where her adoptive parents, Gene and Pat Park, have long had their diner, the Starlight; they need to be out by the New Year, a few weeks away. Will strikes a deal with Annie: if she’ll pretend to be his lawyer for a week, just as a body to show Jim, Will will stop the building demolition and associated evictions. In this lawyer role, Annie unexpectedly gets roped into organizing a high-end sit-down dinner Christmas fundraiser to get Will out of one of those legal messes, something at which she has no experience. Will is roped into helping her, and as they spend time together they start to fall for each other. What if Will is unable to fulfill his end of their original agreement?