 If you liked
Air
|
 ...then you might like
Kamisama ni Natta Hi
|
Both shows will make you laugh and cry. They start out deceptively normal (for an anime) and then the Key twist shows up and drives a knife into your heart. A lot of characters in both shows are surprisingly mature, deliberately acting out for the giggles. The main message, when you're done with the show, is actually rather somber.
"Air" has better pacing and script, which is helped by the rather sparse day-to-day existence in the settings it depicts. "Kamisama..." is actually quite relevant to modern life but the same modern setting makes it comparatively cluttered in terms of everything that gets included in the story.
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The Day I Became A God and Air are two anime produced by Key, a visual novel company known for Kanon, Clannad, Little Busters, and Angel Beats. Both anime are about a boy meeting a younger girl with a somewhat quirky personality and the summer they spend together. There are several other characters the main character meets who share a bit of their own stories with him as well. Watch either of these if you would like some sad moments (especially more present in Air), comedy (especially more present in The Day I Became A God), and decent animation.