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Toughest lessons the mane characters learned in the series

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In many episodes, the mane characters (whether it's the Mane 8, CMCs, or Discord) learn a valuable lesson. Sometimes, the lesson is standard and/or learned proactively. Occasionally, they learn it the hard way, and how they learn that lesson can be really difficult to handle.

The one that comes to my mind immediately is Twilight from Amending Fences, and I still maintain it to be the hardest any of the M8 learned in the show. For so long, Twilight's mirrored image withheld her grief and pain because someone she felt she can trust and connect didn't take friendship so seriously in favor of over-studying. Each time Twilight tried to reconnect with her and make up for the terrible thing she did, Moondancer continued to reject every attempt at friendship, because the pain was so deep. Twilight's attempt to recreate the party she voluntarily skipped was her breaking point; MD finally let out the torment she suffered since devolving into a recluse. To make it tougher, Twilight had to watch her break down and cry, adding to the regret Twilight already felt leading up to it. Had she not develop and become the Princess of Friendship, Twilight might not have absorbed all of Moondancer's grief, but TS needed to hear MD's pain and absorb it so she could truly comprehend what it was like to be in MD's shoes.

Can you come up with any other tough lessons the mane characters learned? If so, which ones, and explain why.

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Fluttershy in Health Of Information learned that if you spend too much effort caring for somebody, you won't be able to care for them at all. Self-care is important too.

I feel like this is a lesson that probably applies more to older viewers: people who may have experienced caring for a pet, or a family member, and maybe pushed themselves too far at times.

I'm sure there were other hard lessons, but this was the first one that came to mind.

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37 minutes ago, GlitterCat said:

Fluttershy in Health Of Information learned that if you spend too much effort caring for somebody, you won't be able to care for them at all. Self-care is important too.

I feel like this is a lesson that probably applies more to older viewers: people who may have experienced caring for a pet, or a family member, and maybe pushed themselves too far at times.

To add to what you wrote, how she learned this lesson makes it stick. Twilight never caught the dangerous disease, because she had a good night's sleep, while FS spent all night reading and researching. Even as swamp fever rapidly progressed through her system, she continued to press herself to get that honey, and almost died from it.

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