Spoiled single girl Angie Moore (Liliana Tandon) is living the good life in New York City - shopping, eating at the best restaurants, and no job to go to Monday Morning - all on her mother's dime. But when her frustrated mother, Margaret (Lorraine Bracco), cuts Angie off 25 days before Christmas, Angie is determined to continue her lush lifestyle. Three years earlier, Angie's father Graham (Michael Gross) bought her a special antique snowflake ornament as a reminder of having it all isn't about when you own, but who you are in your heart. Angie receives a call from her parent's attorney Naresh Kumar (Pankaj Tandon) who thinks Angie is her sister Sophia (Kate Avallone). Angie learns that there is a sizable trust that she will inherit once she gets married. Angie decides to find a man to marry by Christmas, a plan her friend Paulette (Kate McGarrigle) fully endorses. They call a number of men that Angie listed as potential mates without success. Then Paulette discovers Tyler Davis (Charles Hittinger) on Angie's Facebook page. Tyler was the quarterback and most popular boy in Angie's high school. Angie heads back to her small hometown of Greenwood, a town she hasn't been back to since her father died two years before, with her sights set on her high school crush, heartthrob Tyler, As Angie drives into downtown Greenwood, her car dies. Gabe Hudson (Dean Geyer), Tyler's best friend, is working at his father's diner and notice her trouble. He calls a tow truck for her and serves her a plate of pancakes he made. Angie spills coffee on herself just as Tyler enters the diner and flees. Gabe invites Angie to a Christmas party at McMillan's the following night as she unpacks her luggage from the broken-down car. Angie arrives at home and her mom Margaret, the mayor of Greenwood, is happy to see her home for the Christmas season. Sophia stops by to see for herself and tells Angie she hasn't needed her parent's funds for years. Angie visits her old elementary school to see Mrs. B (Livia Treviño), her former teacher. The afterschool class learns Angie is a "consultant" in New York City. Mrs. B reminds Angie how inseparable Angie and Gabe were in grade school. She also tells her about how Gabe and Tyler continue to volunteer time at the school. Mrs. B gets Angie to agree to help tutor some kids in math after school. Angie sees Krissy (Kiara Pichardo) in her own clothing store with daughter Penelope (Emilia Faucher). In her new red dress, Angie finds Tyler at McMillan's. He barely remembers her as the smart girl and Raj (Shawn Jain), another classmate doesn't remember her at all. Tyler reveals he has a dream to open a gym and have kids play team sports there. Tyler answers Angie's cell phone and learns about the trust fund and Angie's scheme to marry him from Paulette. Gabe drives Angie home to her family's palatial estate. The next day Paulette called to check on Angie's progress with Tyler. Later, Angie is at school inventing word math problems for the students. In the hallway, Angie and Tyler have an awkward conversation where Tyler invents an excuse why he had to leave the party the night before. Meanwhile, Gabe's father Barry (Robert Walsh), tells Gabe the diner might have to close if business doesn't improve. Angie enters and offers to look at the financial records and help Gabe in any way she can. After some time with the books, Angie makes some recommendations regarding personnel and budgeting. They also agree people have forgotten what Frank' diner is all about. Angie suggests they sponsor a charity dinner for the less fortunate on Christmas Eve. Gabe does not think the diner can afford the event. Then he has Angie don an apron and have him help in the kitchen learning to cook. When the evening is over, Gabe confesses how hard it has been for him to come back and get the diner going on the right path again. Angie says that her father would be disappointed in her too being downcast during the Christmas season. The next morning, Angie calls her friend Suzanne Park (Rachel Kent) whose firm hires new culinary talent, and tells her about Gabe's fabulous cooking. She invites Suzanne to her family's Christmas party the Gabe's diner is catering. Tyler texts Angie. When they get together, he reveals he learned about Angie's scheme for marriage from Paulette and that he agrees to do it in exchange for helping him start his own business. Angie excitedly calls Paulette with the news knowing she is going to marry the hottest guy from her high school. At school that day, Mrs. B tells Angie about Julia Newton (Kathy-Ann Hart) of Healthful Foods and the charity work they do to help the less fortunate. She also tells her that she will be at the tree lighting ceremony in the town square. Angie says with her mother being the mayor, she is not allowed to miss it. That night the tree is lit and Tyler uses it as the opportunity to publicly ask Angie to be his wife. She is stunned but says "Yes". The Moore holiday party turns into an engagement party for Tyler and Angie. When guest chide Angie and Tyler to kiss, Angie runs off to check on Gabe. Gabe is aloof and seems disappointed he is catering an engagement party. At the end of the party, Suzanne Park recruits Gabe for her restaurant development business. Gabe is surprised that Angie asked her for this favor. The next day Angie's mother questions the need for Angie and Tyler's to get married so quickly. Their conversation is interrupted by Gabe who thanks Angie for connecting his with Suzanne. He shows her a Christmas tree that they obtained at the Community Center where the diner's charity dinner will be held. They decorate it together and Angie includes the ornament her father gave her to finish it off. As Tyler adjusts the star on the top, he bumps into the snowflake and it falls to the floor and breaks in several pieces. She leaves the hall in a hurry. Tyler tells Gabe that he is happy his life is finally coming together and is thankful to Angie for making that happen. In a phone conversation with Paulette, Angie is regretting the scheme she put in place and deceiving the guys. Paulette counters that this is the happiest time in her life. Angie says if this is the happiest time in her life, she is in big trouble. Gabe tells his dad about the opportunity in New York City that Angie provided, but his dad pressures him to stay until the diner is operating smoothly again. At school, Mrs. B takes Angie aside and tells her she is surprised she would marry Coach Davis. As Angie and her family prepare wedding invitations, Sophia gets a call from the attorney about the wedding trust. Paulette arrives to make sure Angie doesn't get cold feet before the wedding. Gabe rings the bell and reports that he can't afford to do the Christmas dinner at the Community Center. Then Angie is trying wedding dresses. She can't decide on any even though the perfect dress appears. Sophia corners her and tells her she knows about the wedding trust, but informs Angie to inherit the trust, she needs her mother's approval of her and her choice for a husband. Sophia suggests to their mother that they invite Tyler to dinner. At dinner that night, Angie's mom hosts a gingerbread house competition. The newly engaged couple wins. Tyler creates a story of how he was overwhelmed when he saw Angie in her red dress at McMillan's Christmas party as the spark that led to their engagement. When Gabe, Raj and Tyler and toasting the marriage at a bar, Raj tells Gabe about the arrangement Tyler has with Angie. Gabe walks out. That night, Angie asks what her mother thought of Tyler. Her mother comments its not who she pictured that Angie would be with. It gives Angie second thoughts and just as she is about to leave to find Gabe, he meets her at the door. Gabe tells Angie that she isn't the person she used to be. Angie used to have goals and a desire to help people. Gabe storms off. Angie lies down and dreams she has a chat with her father. He assures her that even though it will be difficult, she knows what to do. Angie heads to Krissy's store with armfuls of her belongings to sell to support the Community Center Christmas dinner. Krissy and Angie work during a busy day at the store. Julia Newton drops in. Angie challenges her to participate with sponsorship of the dinner and Mrs. Newton agrees to send her truck by with whatever they need. Angie rushes over to Frank's Diner to tell Gabe of her success, but does not want to interrupt him when he sees him flirting with a female customer. Suzanne calls Angie with a job she might like to pursue, a consulting firm needs someone to help with struggling businesses. Angie decide to interview before the wedding. At the afterschool class's Christmas party, some of the class help Angie practice interview questions. At the interview, Angie describes the experience she has had consulting since she returned to Greenwood, and how she is now wanting to stay in the area and pursue the job. The interview team is impressed and Angie is offered an entry level job. On Christmas Eve morning, Angie is dressing for her wedding. Healthful Food surprises Gabe by delivering food for the Christmas Eve dinner. Julia Newton tells him that Angie is responsible. Gabe quickly runs off to Angie's house. Paulette intercepts him on the way to see Angie. She agrees to give him the present Gabe has brought, but tells Angie the present is from Tyler. It is a pendant on a necklace made from the broken Christmas ornament. When Angie sees it, she is sure she in marrying the right guy. After she walks down the stairs and the aisle in her home, she thanks Tyler for the necklace. Tyler admits the gift is not from him. Angie returns her ring saying that she can't go through with the wedding. Tyler says he knows that she is in love with Gabe. Tyler tells Angie that Gabe is in love with her too. The girl Angie saw with Gabe was his cousin. With both Tyler's and her mother's blessing, Angie throw the bouquet and hurries out the door. Angie runs into the Community Center where Gabe and his crew are setting up the Christmas dinner. Angie admits she lost herself after her father died, but found herself being back in Greenwood, being around her family, and in falling in love with Gabe. Gabe says he loves Angie too. He then says they should get married. Surprisingly, Angie rejects the offer, saying she doesn't want some Christmas deadline dictating their wedding. Angie helps Gabe serve the Christmas dinner. The mashed potatoes look very sticky, but a good time is had by all.