 If you liked
Air
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 ...then you might like
Princess Tutu
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Although Air is deeper in emotions and Tutu is on the lighter side, I feel both heroines encounters difficult hardship at times. Both animes really touches my heart.
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Recommended by drastikhate
I find the strongest reason to recommend an anime is the feeling you get from watching it. While Princess Tutu and Air are quite different in setting and style, I got that same feeling of really feeling for the main heroine in the struggles she goes through.
I'm attributing this to the depth of empathy established in both Misuzu and Ahiru. They are both in incredibly unfortunate circumstances and have to overcome predetermined rules to succeed.
So, if you liked Air or Princess Tutu because of the feeling you got from watching them, I'd recommend the other to you.
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Recommended by Kamio-chan
Both focus on a ya cast as well as having elements of somberness to it and supernatural elements and also lots of nice to look at art and character designs.
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Recommended by Disapeared_Ghost
Princess Tutu and Air are two well-animated shows that start out lightly, but take on darker and possibly tragic directions as they go along. The main character in both series try to help the other main characters, and you can't help but feel bad for the female leads in both of these shows. The soundtrack in both of these anime are wonderful as well.