Christmas is believed to be a magical time when angels roam the earth bringing messages of hope and tidings of good cheer. Kelly Benson has spent the last five years hiding in Chicago after her crush, Gabe, brought a pregnant wife home to Shiloh. She moved to Chicago with hopes of landing her dream job but ended up settling for a job that merely pays the bills. Depressed and hopeless after being fired a week before Christmas, Kelly wishes for a Christmas Angel to come to work its magic. Gabe is raising his four-year-old daughter, Michaela, alone after his wife of five years moved to Tampa with her boyfriend. A week before Christmas, which is also Michaela's birthday, Gabe receives his final divorce decree. Then his ex-wife cancels plans with Michaela for a trip to Paris. Gabe is grumpy and ready to restart the "He-Man Woman Haters Club." Will a Christmas Angel appear to point Kelly in the right way? Can the magic of Christmas drive the loneliness and sorrow away?