Killian Jones, the son of an extremely wealthy family, doesn't properly understand the meaning of life. He's considered the playboy of the high school, and almost all of the girls swoon over him. You could say anyone would want to be him. But it's only until Emma Swan moves to town that everything changes for him. She's poor, in the foster system, and is an outcast amongst other girls. She's not even Killian's type. His best friend dares him to get her to go out with him and kiss him by the end of the month, but things take a sudden turn. The unsuspecting Killian does not realize how high her walls are built up. Will he be able to tear them down and win her heart, or is there such thing as setting the bar too high?