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If you liked Kaleido Star add

...then you might like Glass no Kamen (2005) add

We watch our main characters (Sora and Maya) start their journey into entertainment. For Sora, it's the circus-like Kaleido Stage. For Maya, it's taking the theater and acting world by storm. Watching Glass Mask immediately invoked Kaleido Star for me, which I had watched years ago. Both series follow a similar structure - moving from play to play in Glass Mask, and from stage to stage in Kaleido Star, with lots of character drama and personal growth in between. Both series are from the early/mid-2000s and invoke the same nostalgic feelings I have for the era. They also have similar running-lengths that are hard to find nowadys where everything is split into cours. I highly recommend both of these shows!

If you liked Gintama add

...then you might like Urusei Yatsura add

Aliens, wacky characters, slapstick antics, very funny. Gintama can get more serious at times, and Urusei Yatsura can focus more on romance, but both are shows I can sit down and enjoy with a good laugh.

If you liked Toradora! add

...then you might like Golden Time add

Made by the same people. Both shows are romcoms, and the good kind. Both are very funny but also very dramatic. If you enjoyed one you'll enjoy the other!

If you liked Red Garden add

...then you might like Mahou Shoujo Madoka★Magica add

Both shows have a primarily female cast. The main characters are forced (more-so in Red Garden) to fight beasts/witches, and if they give up they die. Characters don't fully understand the situation they're in for most of the series. They're both pretty dark series, and there are definitely some more similarities.

If you liked Shoujo Kakumei Utena add

...then you might like Ouran Koukou Host Club add

Ouran and Utena share a lot of similar things. Crossdressing protagonist? Check. Lots, and lots or roses? Check. Gorgeously designed academy for wealthy students? Check. The main difference is Ouran is more geared for comedy, and Utena is...a bunch of things.