Sarah is an organic farmer who meets a man named Rip Van Winkle Jr., who claims to be from 1787. Soon, she discovers old-fashioned romantic feelings that might be just as crazy as his story.

A runaway bride, Kate, making herself scarce for the holidays, meets a ski patrol rescuer, Jason, at a resort. Her December days begin to brighten, until her parents and jilted fiancé, Alex, show up at the mountain to reset the wedding for Christmas.

Dr. Kate Lawrence, a celebrity relationship expert, plans to publicly announce her engagement to Bryan, a handsome and perfectly polished businessman. As Kate prepares to share the news, Bryan shocks her by breaking up with her and calling off the wedding. Wanting to save her from humiliation and protect her public image, Lucas Wright, Kate’s childhood friend steps in and pretends to be Kate’s fiancé.

Young at heart graduate student Becca strikes up an unlikely friendship with Emily, a quiet girl who recently lost her mother. With every passing play date chaperoned by Emily’s father, Becca helps Emily come out of her shell and cope with her loss, and Emily teaches Becca to take on adult responsibilities. When a romance develops between Becca and Nate, though, the two must learn to balance their new relationship with Nate’s responsibility to Emily, and with Becca’s responsibility to finish her education.