Jessie Patterson is a wedding planner who has had three failed engagements, all of which were called off at the altar. She has now given up on finding true love and is content with casual flings. Meanwhile, Aiden MacTiernan is a successful businessman who has made a bet with his friends that he can find a fiancé in the four weeks leading up to Christmas. He is convinced that he is "marriage material" and is determined to prove it.
When Aiden meets Jessie, he is immediately smitten and begins to pursue her relentlessly. Jessie is initially resistant, but eventually finds herself falling for Aiden's charm and persistence. However, when she learns about Aiden's bet, she becomes wary and questions whether his intentions are genuine.
As their relationship deepens, Jessie and Aiden must confront their fears and insecurities about love and commitment. Jessie must decide whether she is ready to open herself up to the possibility of a serious relationship and risk getting hurt again, while Aiden must decide whether his bet is worth potentially losing the woman he has come to love.
With the holiday season in full swing, Aiden and Jessie must navigate the ups and downs of their relationship as they both come to realize that finding love is not always a simple or straightforward journey. Will they be able to overcome their doubts and fears and commit to each other in time for Christmas, or will their relationship become just another casualty of Jessie's past failed romances?