Vivian Vaye (Vivica A Fox) is a magazine editor who is seeking a Christmas feature article for her magazine, Vibrant. Her assistant Lena Jones (Morgan Dixon) challenges Vivian to assign her the opportunity based on a sample story she wrote that Vivian had not yet read. As Lena waits for Vivian's call that evening, she tells her mother Deborah (Jackée Harry) about the potential job, Lena learns that her cousin is getting married, leaving Lena the only single one in her family for Christmas. Lena heads up to the attic and finds a black dancing Santa her grandfather Clarence was fond of. She also discovers an old painting with a woman named Mary who is not her grandmother, and her grandfather's journal. Lena consults her mother who denies that her father had eyes for anyone but her mother but that her father always talked about life in terms of before and after Pineville, which seems to be the location a photograph of Mary was taken. Lena thinks there could be a story there. When Vivian calls offering her the chance to write the Christmas feather, Lena pitches the last Christmas in Pineville story of romance and mystery which intrigues Vivian. She is very supportive and tries to inspire confidence in Lena. Deborah too also wants to find out more about her father's life. Lena heads to Pineville. Pineville is a mountain town but doesn't seem that cold. Lena stops by a library and immediately meets Mary (Ciarra Carter). There are a lot of Mary's in town. The library Mary she says that the Mary Lena is looking was Mary Payton. She passed away but was a legend in town. The library archives started in 1995, so there isn't much research Lena can do. Mary steers Lena to visit Mary's cafe to ask the family for help. At the Cafe, Lena meets a man named Michael Payton (Alonzo B. Slater), who is the grandson of Mary Payton. Lena tells Michael about why she is in town, and he sets up a date to talk it over while he isn't working at the cafe in a deranged Santa suit. Lena calls her mother for a gingerbread cookie recipe. Lena and Michael bake cookies for the café book exchange. Michael explains that his grandmother passed away earlier that year. Beside owning the café, she was also a teacher and was about education and community. Michael invites Lena over to his place for lunch. He promises to look through his grandmother's things to search for info on Clarence Cobb, Lena's grandfather. Now in normal clothing, Michael tells his father Allen (Asante Jones) about Lena and shows him the photograph he took of the painting of Mary. Michael has a job offer in New York that he is also excited about. In his grandmother's bedroom, Michael finds old love letters from Clarence They will be very helpful for Lena's article. Lena chats with her mother about whether she would want to know if her father had an affair. Deborah prefers to think whatever happened was beautiful and not some torrid affair. Michael's father is not supportive of turning over the love letter to Lena before he has the opportunity to review them. He doesn't want Lena looking into the past and revealing an affair. Vivian calls Lena to check on her progress on the story. She states she is interviewing more family members that day. After Allen and Lena meet and have a long talk, he is willing to release the letters to Lena after he reads them. He is also curious to see the painting of his mother. When he does, he can place the scene of his painting in his own house. Allen and his wife invite Lena for dinner. Michael says he will be late because he has to pick up Stephanie from the train station. Michael turns out to have a girlfriend named Stephanie. Lena is like, "Your what now?" Lena reluctantly goes to dinner with Michael and his family for the story. Stephanie is the worst, but she travels a lot and is gone for the next day. Michael and Lena share the letter from Clarence. Meanwhile, Deborah finds the letters Mary sent to Clarence in a box in their home. The timing of the letters indicate that Mary knew Clarence before she was married. He was working in Pineville on a story and promised to return when he got a job offer in San Francisco. Mary was waiting for Clarence to return. Michael and Lena notice an ornament in the painting that Lena possesses. Michael recognizes it from a hand painted ornament shop nearby. At the shop they meet Otis (David McKnight). They discover it was Otis's brother Wilson whom Clarence was trying to clear from a crime in San Francisco at the time Clarence met Mary. As they sit on a bench, Michael talks about his love of New York, and Lena talks about how nice San Francisco is. Claudia recognizes Michael and stops to say hello. Claudia (Kelli Dawn Hancock), as a young girl, was cared for by Many before she was married. She tells Michael and Lena the story of a time when Clarence returned and got into a dust up with Michal's grandfather Richard. They go to the Christmas tree lot to meet an old friend of Clarence's named Gabe (Arthur Roberts). He explains that when Clarence returned to Pineville, Mary had already fell for Richard. He explained that Clarence was set on living in San Francisco and Mary was never leaving Pineville after Richard came back from the service. Clarence actually gave Mary the painting as a gift but she returned it saying that she already knew what she looked like but if he wanted her to remember Clarence, he should paint a portrait of himself. Ultimately, the story of Clarence and Mary was one of bad timing and change circumstance where other priorities took precedence over their love. At the end of their visit to the tree lot, they secure a tree for the café. Stephanie has no interest in helping with Santa night and Lena offers her services. The family sings Jingle Bells as they decorate the café for Christmas. Michaels mother tells him that he should date Lena because they are destined to be together. Lena writes her story and stays an extra day in Pineville. Lena thinks she is destined to be with Michael and kisses him even though he has a girlfriend. Michael is conflicted, thinking that he and Lena are just like their grandparents, heading in different directions. He comes to the conclusion that even though he still dreams about going to New York, he does not love Stephanie which he admits to his dad. Lena packs her suitcase to leave town. Before she leaves, she gifts the portrait to Mary's family and in return, they give her Clarence's letters. Back in San Francisco, Vivian loves the article and has hired a new hunk personal assistant. Lena gets the promotion staff writer. Lena should be happier than she is because all she wants is Michael now. Meanwhile, Michael and Stephanie break up. Stephanie seems unphased and is going off for a girls vacation to the Outer Banks. Michael's parents are thrilled and encourage him to pursue Lena. Michael shows up in his terrible Santa suit at Lena's family party and tells Lena that he loves her. They kiss and Lena's article closing is read in a voice over.