Jordan Sanderson wins a one month scholarship for artists that may change his life for the better and get him closer to his dreams. His father stands in the way and decides to send him to an all boys boarding school to make him forget all about that "nonsense". Ruby Sanderson doesn't deal well with stressful situations, but she'd do anything for those she loves, that's why when her twin brother asks for a tough favor she can't help but say yes. Watch as Ruby struggles to blend in with all the male company in Woodside, a strict boarding school for boys. Being a girl is hard, but how much harder is it pretending to be a boy?