There's a vibe, a mood, to this show that makes it feel a lot more down-to-earth and genuine than almost any other romance anime. It's hard to pinpoint where that vibe ultimately comes from.
Maybe it's the voice acting. The voice acting for the main character, Rikuo, is not especially flamboyant, but it really captures the nuance of his voice when he casually chats with his friends or when he awkwardly talks with Shinako. The other characters are similarly well-dubbed, and because of that, the character interactions always felt realistic and sincere.
Maybe it's the art, which, while also not especially flashy, is made up of warm, muted colors and pencil drawn-like lines that serves as a direct contrast to the shiny, manufactured feel of many anime today. The style reminded me of older, cel-animated works. The characters were also unique, with distinct looks that matched well with their personalities.

Maybe it's the story, which is set in a very ordinary world where the most unrealistic thing is a trained crow. There's no supernatural occurrences, no insane coincidences, and nothing's over-dramatized. It's a story that puts the focus on the characters and their interactions, and on that front, I think it does very well.
Now, if that was all, it would be fine and dandy, and it might've actually ended up one of my favorite romance anime of all time. It'd be a deep, beautiful story about a guy who picks his life back up and reconnects with old friends, about a girl who learns to accept the past and move on, about a boy who realizes that he can be more than a shadow of his late older brother.
Instead, they introduced one character that destroyed the purity, the humbleness of this show: Haru.

I hated Haru from the start. The first warning sign was that crow. And then we learn that she fell in love with him due to a brief chance encounter. And then we see that she pursues Rikuo aggressively even after he rejects her advances, in a fashion that is very much characteristic of the unrealistic plots of many anime.
And then there was the ending. Rikuo leaving Shinako for Haru and Shinako going with Rou basically threw away all of the character development that was built up over the course of the show. Now, I realize that Haru is not the reason why Rikuo an Shinako didn't end up together, but I would MUCH rather have an ending where Rikuo just ends up single, than one where he, for some reason, thinks that he's now in love with Haru and pursues her. It just didn't make sense. There was no lead up to this, no real reason why either of them would catch feelings. Besides, the name of the show, "Sing Yesterday for Me" remains unresolved.
Maybe this ending doesn't make sense because real life and real relationships don't make logical sense either. In real life, people don't just manage to stumble upon their soul mate and then live happily ever after. Frankly, even without Haru, none of the possible endings would have been completely satisfying. Rikuo and Shinako just didn't feel right together, but nor did it seem like they should be nothing more than friends. That's just how the characters were built up.
However, I find the ending they chose to be the most infuriating possible. It'd be fitting for the ending not to be completely satisfying, but they didn't have to bring down so much of what had been developed beforehand along with it! Ultimately, this is still fiction, and good fiction has purposeful writing. This just didn't cut it.
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