Privileged (2008)

S1E3 All About What You Really, Really Want

When Rose learns that she has to redo her freshman year because of her low grades, Megan takes it upon herself to speak with the headmaster in hopes of securing a second chance for her friend. During their meeting, an unexpected chemistry develops between Megan and the headmaster, leading her to agree to go on a date with him. This new romance stirs feelings of jealousy in Charlie, who can't help but feel uneasy about the situation.