Young Americans (2000)

This series portrays life at Rawley Summer Academy, an elite school in Connecticut where boys with a bright Ivy League future spend the summer industriously in classes and rowing training on the lake. It's mainly told from the viewpoint of Will Krudski, a gifted, genuinely inquisitive student and future writer, who feels guilty having cheated at the entry exams. His roommate, Scout Calhoun, is a school legacy who makes an effort to become friendly with some underprivileged local kids and falls in love with the daughter of a garage owner who turns out to be family. Most of his classmates are golden spoon boys, but still have their problems, among each-other, at home and sometimes with the locals. Actually Jacqueline 'Jake' Pratt is a girl pretending to be a boy as the only way to get in, causing great confusion for Hamilton, the school dean's son, who begins to fall for her.