Chance DeLuca liked to think he was great at everything. He was team captain of the Maybanks' men's hockey team, the Bulldogs. He had good grades and was the life of the party. He would even consider himself a great boyfriend. That however becomes abundantly unclear after his girlfriend breaks up with him. Now he is determined to win her back after he has learned how to be the perfect boyfriend. One fake date leads to another and soon Chance finds himself wondering if being the perfect boyfriend for someone else is what he really wants. For Winnie Harper, dating has never been easy. Her love life is close to nonexistent. Dating had never been a major priority in her life, but after watching her friends fall head over heels in love, she begins to wonder if that kind of love will find her. What does find her, is a desperate offer from a boy who resembles a childhood crush of hers. Perhaps fake dating each other will help them prepare for who they really want. But what if who she really wants is him?