 If you liked
Ouran Koukou Host Club
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 ...then you might like
Hayate no Gotoku!
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First off, let me just say that both Hayate no Gotoku and Ourah High School Host Club are zany, random, and absolutely hilarious shows. I\'d say they\'re a definite must watch if you\'re into comedies.
How are they similar?
Hayate no Gotoku has our hero, Ayasaki Hayate, who becomes a \"combat butler\" to pay off his debt to Nagi, who paid off his outrageous debt to some Yakuza; Yakuza of whom his parents borrowed a ton of money from, lost said money in gambling and crazy dreams, and then decided to skip town and leave Hayate behind with the debt. Boy is HnG a whacky show...
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Both are about high school students owing a debt to rich kids, and both the main characters are clueless about the people that have crushes on them. Although Haruhi in Ouran High School Host Club has no choice but to cross-dress, Hayate from Hayate the Combat Butler (Hayate no Gotoku) is forced to cross-dress at alternate times by his master and his master's maid (I find that somewhat similar). Both of these are very random, and have awkward situations, although Ouran High School Host Club is shojo and Hayate the Combat Butler is shonen, I think they're both great. And hilarious. XD
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Recommended by Melancholy42