Emma Reynolds is a newly minted junior partner with a New York City law firm and who followed in her father's footsteps career-wise, although Emma only knows her clients as faceless corporations, while her father, who had his own practice in the family's longtime hometown of Oliver's Well, Virginia with his friend and partner Joe, knew the names and faces of everyone with who he did business. Always too busy with work and now a bona fide big city girl, Emma has headed home to Oliver's Well this Christmas for the first time since law school, what could be considered one year too late as both her father and mother, Cliff and Caroline Reynolds, have passed away this year, meaning she didn't get that one last Christmas with them. Emma will be spending this Christmas with her Oliver's Well-based siblings, Andie, a successful novelist, and Daniel, a caterer, and their respective families as the three siblings will be closing up the family house on Honeysuckle Lane, including figuring out what to do with the family heirlooms and mementos, before putting the historic house and the appropriate other items on the market. The importance of this Christmas is honoring their parents' memory, they who loved Christmas and were each other's one true love for the duration of their fifty-three year marriage, it being love at first sight. Emma has come to town solo, delaying telling her siblings that she and her longtime boyfriend, cardiologist Ian Tillman, who they expected would be an imminent part of the family, have split. One of Emma's responsibilities ends up being to find someone to help them appraise the items in the house. Who Emma hires is ex-Harvard History professor turned antiques dealer Morgan Shelby, his hiring despite his and Emma's antagonistic first meeting. In going through specifically Caroline's antique Victorian desk - it where she used to hide many of Emma's Christmas presents - Morgan finds hidden some love letters written to Caroline from someone not Cliff - the letters signed "R.J." who apparently was engaged to Caroline before Cliff. Not wanting to upset the apple cart before knowing what it all means, Emma and Morgan, without telling either Andie or Daniel, go on a mission to discover who R.J. is and what he meant in Caroline's life. In going on this mission of discovery, both Emma and Morgan may come to some realizations about what they truly want in life, Emma's which includes facing the real reason she left Oliver's Well and which is made all the more difficult with something from her recent past following her to Oliver's Well.