 If you liked
Ouran Koukou Host Club
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 ...then you might like
Kuragehime
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The whole atmosphere of the show is very similar and so is the humor. They're both very carefree and easy to rewatch. They also feature a similar kind of romance - starts out as friendship. Also, the main heroines are both very similar, rather quiet and intelligent. Although Haruhi seems more reserved at times.
Both series have the same atmosphere, though the crossdressing and the stories are rather different.
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Recommended by kagamishinigami
Kuragehime is Ouran in a way.
Kuranosuke is very similar to Tamaki in terms of personality(other than the cross dressing part)
Tsukimi is well Haruhi as she does not really care around things and thinks of Kuranosuke as weird.
as for the storyline both are similar as Ouran deals with things happening in the Host club while Kuragehime is about the happenings of the Amamizukan
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Recommended by yagamisignum
They both are romantic comedies with a hilariously funny bunch of characters that will make you smile throughout the series. Oh... And did I mention that they both have cross-dressers as the main characters? Of course I didn't. LOL! Anyway, Kuragehime isn't as random as OHSHC, but gives you all the chuckles you need.
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Recommended by Silverfang18
Main character is not use to the fancy lifestyle but over time comes to terms with how it is to live outside their comfort zone.
The humor is very similar if you ask me. One in a more down to earth and the other not, but they makes me laugh just as much!
They both also have the most dreamy fashion ever (❁´▽`❁)*✲ﾟ*
(They are both my nr 1 top favorite animes ever!)
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Recommended by SwediCandy
Both are female lead slice of life comedy shoujo, and are tonally very similar. Both heavily feature cross dressing as a major plot element. They're both a good notch above most stuff in their genre quality wise, but nothing too amazing. Most people who like one will probably like the other.
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Recommended by Chromephone
Both light-hearted and hilarious, a bit of a parody (more Ouran that Kuragehime), with interesting characters that have great chemistry! Also, both have underlying substance to the story amidst all the comedy presented in a way that's not cliche and is highly entertaining.
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Recommended by fullmetalbender
-Cross dressing main character
-Relatable protagonist with a sad backstory
-Heartwarming
-Dorky humour
-Cute Romance between unconventional characters
-Flirty Charmer/ Studious Awkward-type dynamic
-Up for interpretation relationship
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Recommended by weeaboogers
Both are sweet romantic comedies with cross-dressing main characters and occasional forth-wall breaking. Kuragehime spoof otakus in a fashion similar to Ouran's spoofing of shoujo tropes, and both have fairly plain-looking, intellectual female protagonists. Both also have catchy soundtracks.
Both are super female centric, both have similar stories of girls trying deal with crazy people around them in order to make a dream come true.
Both series have this upbeat and comforting vibe to them which makes them a pleasure to watch. Another key detail is they both include crossdressing main characters who need to hide their true identity from others.
They're also both shojo romance series :)
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Recommended by ughitsmaxxie