 If you liked
Nana
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 ...then you might like
Koizora: Setsunai Koimonogatari
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Both Koizora and Nana are dramatic stories. The characters in Nana are older-but they go through similar things. The main character in Nana, Nana Komatsu, acts similarly to Mika, the main character of Koizora. They both involve tragedies such as unplanned pregnancy and saying goodbye to the one you love.
They're also both two of my favourites. ;)