Elliott (Eli) and Samantha (Sam) are roommates at Gallagher's School for the Elite (really just a fancy way of saying boarding school for the rich). Sam goes home with Eli for winter break, where she meets his lovable family, and a misunderstanding leaves Eli and Sam with no choice but to pretend to be engaged. Will they end up falling in love? Or will their fake engagement follow plan and end in a divorce?