 If you liked
Ouran Koukou Host Club
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 ...then you might like
Diamond Life
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She's just a poor girl and he's just a rich boy. How ever will they meet and fall in love? Ouran is much more light hearted and happy go lucky while Diamond Life deals with heavy topics such as business, finances, and something else I can't mention due to spoilers.
Haruhi and Kanae are both strong, mature, inspiring women who are capable of taking care of themselves and keeping their pride. While both gals earn back their debt, they change our rich boys perspectives on life.