I'm writing for those who have lingering questions about whether there is a possibility for a S3. Saddens me to say but the realistic answer to this is it's unfortunately super unlikely, but it doesn't hurt to hope. Some recent examples of reboots bringing in sizeable viewership are Shaman King 2020, Bleach:TYBW, and Fruits basket, which may signal to studios that anime reboots aren't as big a risk as thought previously.
Its always bummed me out that Kimi ni Todoke was never picked up for a s3, and I don't think there's any definitive reason as to why. Could have been lack of viewership, low sales, lack of source material, or a large number of other factors that resulted in it never happening. I do remember thinking at the time that season 3 will pick up soon after the manga starts to accumulate more chapters, and I recall a lot people were anticipating a 3rd season, it being high on their list of potential anime to return. All that to say, I don't think viewership was the biggest issue.
There were also a lot of other anime during that time that never got picked up after their first season despite their huge popularity, like Ao Haru Ride and Usagi Drop. This may be a bit of a generalization, but modern shojo manga rarely get their full story covered in an anime, nevertheless two adaptations - original and reboot. Unfortunately, japanese studios don't think of shojo the same way as shonen. Shonen are long-running, 20-minute affairs that occur alongside their manga to boost viewership, and shojo historically tend to hover around the 12-24 episode mark, with the hope that viewers will tune into the manga afterwards.
Fruits basket is a really really rare case. Bleach returning was never suppose to happen and may only have due to interest from Disney. Shaman King returned as a 25th anniversary special. In most instances, anime reboots are an incredibly special occurrences.
Some last predictions on my part. Last decade we saw a boom in reboots for movies due to nostalgia. This decade we're seeing streaming sites bring back shows many of us grew up with (as both reboots and sequels), and to large success. With this years crunchyroll and funimation merger I think there's a possibility for something to change in the space to give rise to older shows being rebooted, especially considering the boom in popularity both anime and manga have received this decade. Unfortunately the rights to anime and manga are a harder sphere to work in as they operate more closely to that of western movies based off novels. Even still, maybe we'll see a huge surge for nostalgia for old shojo anime/manga? Maybe netflix/disney or even crunchyroll will step up to the plate and purchase streaming rights for sequels and spinoffs. Crunchy roll originals have been an interesting exercise in producing webtoons and other non-japanese properties, perhaps we'll see them work on sequels to shows that were swept by the wayside like Kimi ni Todoke. I don't imagine that to be the case as the new stuff has always taken precedent, but I'm hopeful that shojo anime adaptations won't just fade into obscurity after their first season like it has in the past.
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