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Total Recommendations: 3

If you liked
Princess Princess
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...then you might like
Maria†Holic
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You could call Princess Princess the brother anime to Maria Holic. The two anime involve crossdressing, are set in same-sex schools as well as having shounen ai and shoujo ai hints. Although both anime may have these hints there is actually nothing concrete from these genres, at most, a kiss.

Maria Holic, set in an all girls Catholic school could be considered a 'black comedy' since the main character Maria, is known to be a sadistic cross-dressing boy who bullies the bonafide lesbian and focuses on the idea of homosexuality a lot more whereas Princess Princess is more of an all-round comedy that deals with the boys' problem of having to crossdress for the sake of the all boys school they attend.

Neither shows are particulary groundbreaking, but they provide decent entertainment.

If you liked
School Rumble
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...then you might like
Baka to Test to Shoukanjuu
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Filled to the brim with stupidity, over the top antics and plenty of randomness; School Rumble and Baka to Test has much to offer, especially in the comedy department.

Baka to Test is for those who like parodies, and the clichés of anime all thrown into one bag and mocked out of.

School Rumble consists of many "short episodes" of gags, as to not bore the viewer whereas Baka to Test has a certain theme or direction of an episode e.g. the classic "Pool Day"

Either way, if you like brainless laughs and just want something over-the-top and insane to watch then try Baka to Test or School Rumble.

If you liked
Gravitation
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...then you might like
Komatta Toki ni wa Hoshi ni Kike
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They are perhaps two of the longest shounen-ai's out there as well as being downright hilarious and simply entertaining. Gravitation is more fast-paced, to match its setting in the celebrity lifestyle and music industry. It's for people who like silly gags, zany characters and dark back stories. Komatta Toki ni wa Hoshi ni Kike is a lot more slow paced and is easy to appreciate with its slice of life approach. People who like sweet romances will easily fall in love with this. The main love interests in both shounen ai's share a similar trait: they don't have a great start, often at each other's throats but then changes (quite rapidly for Gravitation, and very slowly for Komatta) into mutual understanding and perhaps love.