In high school, Chris Brander had the ultimate crush on his best friend, Jamie Palamino. After being friend-zoned, Brander grew up to be a successful music producer and womanizer. During a trip back home for the holidays, he comes face to face with the girl of his high school dreams and is determined to finally win her over and no longer be just friends. Anyone who has been sentenced to the friend-zone will relate to this romantic comedy starring pre-DeadpoolRyan Reynolds and Amy Smart.