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If you liked Pump Up add

...then you might like Watashi no Shounen add

Both depict a relationship between an assertive girl and a very innocent, feminine boy. Mizutama and Mashuu resemble each other in their sincere, kind-hearted, yet slightly oblivious personalities. Pump Up! is a light romance whereas WnS is a more reflective and ambiguous drama, however.

If you liked Yokohama Kaidashi Kikou add

...then you might like Watashi no Shounen add

Both feature a younger male/older female pairing (though with less of a focus in YKK). Though WnS is far more dramatic than YKK, both are delicately-told stories with themes of growing older, the passage of time, and changing one's perspective through life's stages.

If you liked Otoyomegatari add

...then you might like Watashi no Shounen add

Both depict a relationship between a young boy and an older woman in a very nuanced, respectful way. Otoyomegatari is overtly about a budding romance whereas the characters in WnS are more ambiguously affectionate. Both feature some very tenderly written and emotional drama, as well.