It’s gotta be The 100 Girlfriends Who Really Really Really Really REALLY Love You. Starting out, you wish you were Rentarou. By the time you’ve finished the first couple season you’ll just wish you were dating him instead.

Reverse? Ouran is a classic for a reason. Btw, for those who don’t know the Ouran anime doesn’t even cover half of the manga so I’d definitely recommend giving it a read as well.