Some of these elements remind me of Fox's "The War a Home", with a dad sabotaging daughter's college application because for all of his bluster he doesn't want her to leave home, and son's best friend (Rami Malek!) secretly gay and in love with him. Characters are only as they are written to be, so it's unwise to try to analyze them. That said, my guess is that the boys saying I love you was meant sincerely, but in the beer ad sense, at least for Oliver. It may mean more for poor neglected Cooper. In high school I very much loved my best friend, but it turned out to be in a sibling sense, not romantic. TV shows do like to tease, like with Sue's guy friend in "The Middle." As for Oliver and Cooper, place your bets, but don't bet the rent.