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If you liked Air add

...then you might like Summer Pockets add

It's unlikely that anyone familiar with Key and who has watched both anime will miss the similarities between the two. Both originated as visual novels, and their stories take place during summer on a sparsely populated island. Both main characters have complex relationships with their mothers, and both main characters die. Neither has the happiest ending in the world, but Air is more tragic and shorter, while Summer Pockets is a bit gentler but longer, with more well-developed and captivating secondary heroines compared to Air.

If you liked Bakemonogatari add

...then you might like Summer Pockets add

Both are stories with supernatural elements involved, and both are slow-paced stories focusing primarily on dialogue and interactions. Bakemonogatari has a more developed and realistic writing style, while Summer Pockets attempts to evoke a sense of nostalgia with each character.

If you liked Seishun Buta Yarou wa Bunny Girl Senpai no Yume wo Minai add

...then you might like Summer Pockets add

Both are stories focused on the supernatural, where the male protagonist helps each girl with a different goal. However, in Summer Pockets, there are more romantic and friendship connections, while Bunny Girl is more realistic, and romance isn't necessarily with all the girls. Furthermore, the main heroines, Mai and Shiroha, have complicated relationships with their mothers, and the story explores this aspect.

If you liked Orange add

...then you might like Summer Pockets add

Both are anime where central characters travel through time and try to prevent the central characters of that timeline from committing a tragic act: In Orange, the group of friends from the future try to prevent his death in an accident in the original timeline, In Summer Pockets, Umi tries several times to go back in time to try to prevent Shiroha from having her as a daughter and thus preventing her death.

If you liked Yosuga no Sora add

...then you might like Summer Pockets add

Both are time-travel stories where the protagonist experiences romances with different girls before settling on the main character. However, they have different premises. While Summer Pockets focuses primarily on summer vacations and the connection between the characters in a lighter yet still exciting way, at a slower pace, Yosuga no Sora is more objective and daring. Its romance isn't necessarily with a stranger, but rather with the protagonist's sister, and it doesn't shy away from showing intense scenes. The similarity lies mainly in both being adaptations of visual novels and the way the romance unfolds with each character. So, if you miss time-travel romances with multiple girls while watching Yosuga no Sora, then Summer Pockets will be a great option, though less intense and daring, and more sweet and emotional.