Four Christmases and a Wedding (2017) on Netflix

Chloe plans the first Christmas Fair where she meets Evan and falls in love, but he goes to Norway for his dream job. He bring someone else to the second one; during the third one, Chloe is dating Ted. What will happen this year?

"When event planner Chloe (Kebbel) is hired to plan the local Christmas Festival, she is beyond thrilled to embrace the challenge. Professionally, everything is going great, but much to the dismay of her mother (Post), Chloe confesses she has given up on ever finding Mr. Right. That all changes the night of the opening of the festival when she meets Evan. The two begin a whirlwind romance, but as Christmas Day nears, Chloe learns that Evan is being transferred overseas for work. What follows is three more Christmases where Chloe and Evan cross paths at the annual festival, but each year something--or someone--stands in the way of true love. Will a touch of Santa's magic on their fourth Christmas Eve finally bring them together?"

—Lifetime

Chloe Taylor and her mother Anna are all the family each has had since Anna divorced Chloe's father. They traditionally spend Christmas together at Anna's house in the northeastern-US town of Fairmont. Chloe works for the event-planning firm RSVP and is the lead planner for Fairmont's first-ever Christmas Fair, which will culminate in a Christmas ball. Chloe has also decided to stop dating, not wanting to place any pressure on herself to fall in love. That spontaneous magic of love seems to work for Anna, who reconnects with her high-sweetheart Russ Peterson, a vendor at the fair. It also seems eventually to work for Chloe as she immediately falls for Evan Mathers, in town visiting his sister Kate and Kate's adolescent daughter Sara, and he seeming to fall for her in return. Their first magical night topped with their dance at the ball might be all there is as Evan announces that he is leaving the country indefinitely the day after Christmas for an overseas work assignment he cannot turn down, as he was the one who requested the transfer from their New York office. Over the subsequent three Christmas seasons and Christmas Fairs, Evan always returns to Fairmont to visit Kate and Sara, but something seems to conspire against Chloe and Evan getting together. Chloe must decide if she "settle for second-best": her co-worker Ted, a sweet man who has long pursued her; or if she will wait for true love, with Evan or someone else, that true love which she knows exists; she sees it being Anna and Russ.

—Huggo