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If you liked Skate-Leading☆Stars add

...then you might like SK∞ add

Both have a firey red headed protagnist and calm and cool blue haired character. Both animes include pretty boys who love what they do but try so hard to compete with blue haired character who simply has natural talent. Which almost stops them doing what they love but not quite.

If you liked Free! add

...then you might like Skate-Leading☆Stars add

If you liked Free, i'm absolutely sure that you'll love this anime. The characters aren't similar, but the vibe and feel of the show is. A bunch of pretty boys, training to do what they love. (Reminds me of yet ANOTHER show). Oh and this is one of the only animes where all of the characters look both female and male at the same time.