 If you liked
Hayate no Gotoku!
|
 ...then you might like
Himegoto
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Both are comedies about the main character as a boy who frequently cross-dresses, and has no-face parents who put their son in unimaginable debts, and are chased by debt collectors. They both end up falling into money, and end up working as a gofer for the people who saved them from their debts.
The only difference would probably be the contrast in length. Hayate no Gotoku is a full-episode series spanning multiple seasons, while Himegoto is currently only one season, with only 4-minute shorts.
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Recommended by Estoy_Gordo