After being unceremoniously evicted from her craft shop right before Christmas, ambitious carpenter Andi Johnson must pick up shifts at her grandparents' bakery to earn enough to sue her slummy landlord. Just trying to make it through the holidays, the last thing Andi needs is a distraction in the form of her brother's best friend-the man who stole her heart years ago only to crush it in front of the entire high school. When her car breaks down in the middle of a snowstorm, she has no choice but to accept the ride home he offers. Reformed bad boy and cutthroat lawyer Winchester Robinson's grandmother refuses to retire and pass on the family law firm until he convinces her he values something more than just his win-loss streak. Discovering his old flame stranded on the side of the road could solve his problem but facing down her protective big brother and his own feelings of unworthiness, might be too big of a roadblock for him to overcome. As the storm worsens, they're forced to seek refuge at Win's family's house, where his Nana is staying for the holiday. Win seizes the opportunity and begs Andi to pretend to be his girlfriend for the weekend to appease Nana's worries, offering to take on her lawsuit in exchange for the favor. Realizing it could be a Christmas blessing, Andi agrees. But Christmas cheer brings back old feelings neither want to face. This holiday season could bring gifts of love...if they can move on from the past and look to the future.