Sam leaves Dean's laptop logged in to some app called "TutorMate" and Dean meets his brother's tutor. Cas helps him with his own work and they strike up a friendship. Before long Dean finds himself growing attached to the cute, clever Cas and flirtatiously suggests they go on a date if he applies himself to his college work. Cas agrees, but Dean discovers his online friend is not quite what he expected. (Or, in which Dean thinks he's met a cute girl and finds out he's actually met a cute boy.)