 If you liked
Hayate no Gotoku!
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 ...then you might like
Yoki, Koto, Kiku.
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These two titles don't seem very similar, but when I read Yoki Koto Kiku, it feels somewhat like reading Hayate.
Both of these titles have comedy, although Yoki Koto Kiku has a dark type of comedy, and they both involve rich kids with some financial matter; a debt in Hayate and an inheritance matter in Yoki Koto Kiku. But the biggest similarity may be just the randomness in each of them.
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Recommended by Chimichoco