Four years ago, Fluttershy reached out hoping to make a friend, and instead was abused by a stranger. In response, she withdrew into herself, shutting out the rest of the world. Now she has some friends, but she still fears most strangers, because she never understood what happened to her when she was a teenager. She wishes she could be less afraid of other Ponies, but how can she when she knows that she was rejected for her own lack of merit?
Maybe she'll kill herself. That would be terrible.
Or maybe, with a little help from Rarity, something entirely different will happen.
This takes place around the 1st of October, YOH 1500 and is canon to the Shadow Wars, being part of the Flutterarc. It may also be considered an unofficial sequel to Bad Horse's excellent (and horribly logical) Fluttershy's Night Out, which in this timeline may be assumed to have taken place in YOH 1496. Fluttershy was 16 then, and is 20 now.
In connection to the main TV series, this would be taking place between the start and the end of "Fall Weather Friends" (which is one of the reasons why Rarity is the friend in whom Fluttershy chooses to confide, as Rainbow Dash is in training). It would take place before "Call of the Cutie," which in turn takes place before Fluttershy Is Free.
(Yes, I flipped the order of "Fall Weather Friends" and "Winter Wrap-Up" -- if I didn't, I'd have to assume that the first three seasons covered 5, instead of 4 years).
Its direct sequel in the Flutterarc is Fluttershy Is Free.
Now has its own TV Tropes page!
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Fluttershy comes to terms with a mistake from her past, and learns how to handle herself in the future, with the help of her good friend Rarity.
When Spike is called away to Canterlot on Royal Business, he expects to have to do something for Princess Celestia. Instead, he winds up being interviewed by Princess Luna and fed a lot of gems. Life can be tough for a young Dragon!
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Rainbow Dash and Fluttershy go to see a butterfly migration. Mid-Season 1, immediately after "Call of the Cutie."