Cara and Ben head back to the snowy and romantic resort where they originally fell in love. This time, they bring along their mutual friends - Megan and Sean. While they hope to rekindle their own romance, they also play matchmaker for Megan and Sean.
As the group enjoys their time at the resort, Cara stumbles upon a jewelry receipt from Ben's pocket. Excited and hopeful for a proposal, she eagerly anticipates Ben's big question. However, when Ben's plans for proposing are ruined by a misunderstanding, the future of their relationship becomes uncertain.
Further complications arise when Megan and Sean hit a rough patch in their relationship. As the couples navigate their different hurdles, they must confront the challenges that come with relationships and learn to communicate and work through their problems.
In the end, the couples must decide whether they are truly meant to be together or if their relationships have run their course. One Winter Proposal is a heartwarming movie about the ups and downs of love and the power of forgiveness and communication.
