After Jessie Patterson (Arielle Kebbel) calls off her third engagement - at the altar! - she swears off serious relationships until she finds “the one.” That is, until charming but chronically single Aiden MacTiernan (Andrew Walker) comes along. Unbeknownst to Jessie, Aiden has bet his friends that he can convince a woman to marry him by Christmas - which is only four weeks away - and Jessie is the target of his bet. As Aiden attempts to court Jessie by first hiring her to decorate his apartment, Jessie looks to her sister, roommate and interior design company partner, Vivian (Kimberly Sustad) as her closest confidant. To complicate matters, Jessie is doggedly pursued by her most recent ex-fiancé, Mike (Sage Brocklebank), who still wants to marry her. When Aiden finds himself falling for Jessie too, will he call off the bet and truly pursue her?
While still mourning the loss of her husband and daughter, recently widowed Ellie King (Natalie Hall) visits her brother Aaron Davis (Greg Vaughan) and his children for Christmas. Ellie does her best to enjoy the holidays, even making new friends with Mrs. Thompson (JoBeth Williams), a local shop keeper, and handsome admirer Deputy Strode (Dylan Bruce). Settling in nicely with her brother's family, Ellie also meets Erik (Bobby Campo), a young man abandoned by his outlaw father whom Aaron has taken in as one of his own. When Aaron travels out of town to purchase adjacent land for farming, Ellie agrees to watch his children, but the season’s festivities are threatened when Aaron goes missing.
