It's Christmas Eve, 2004. Eve Simon is a wealthy and successful advertising executive with Bernstein & Barlow on Madison Avenue, but her personal life is less than satisfying. Beyond her assistant Mandy who has been her best friend since grammar school, her married boss and lover, Neil Barlow, is the only other significant person in her personal life. She has not been home to Eastborough, Oregon since she left eight years ago, and rarely speaks to her loving and supportive family there. When Neil tells Eve that he will be spending Christmas with his wife and kids instead of her as was originally planned leaving her alone for Christmas, Eve reflects on her life, most specifically the decision she made eight years ago not to marry her then fiancé and love, Scott Gustafson, who she has not seen or heard of since, but rather accept the internship with Bernstein & Barlow that began the day after Christmas. Christmas was to be the day of her wedding.