Too Much Time On Her Hooves.

As we saw today, most of Fluttershy's previous problem with Nightmare Night is that she had the time to convince herself it was a big, fat, scary deal; upon actually attending, she realized that while it wasn't really the horror she'd talked herself into thinking it was, it also just wasn't something she was interested in. This made the thing a sort of a call back not only to Luna Eclipsed but also to Green Isn't Your Color. As it was then, playing dressup and making herself look and feel silly just is not her thing and never will be. This means we have a lateral move from being scared by it to ignoring a boring ritual that is not to her taste and hoping it'll go away.

The reason that I mention this is that History teaches us that Fluttershy is the only one with enough time to talk herself into things really. On the one side we have a busy, busy farmer, a busy, busy seamstress with big plans, a weather controller training to join a reserve force of the military, a bakers' apprentice who's always on the go and a high-ranking noble who's pretty much a whirling dervish of self-improvement. On her side, we have the local hayward, tasked with feeding tame wildlife and controlling critters that become a mild nuisance to agriculture. She has plenty of leisure time to psyche herself into being afraid of things. Also, I think that she has a family member to help with that. This is because I think that one of the three bully ponies who harassed her as a filly is her older brother. The shmuck Hoops looks too damned much like her to be anything but Pony Pretending To Be Mike Patterson and thus looks good as the sort of shite-poke who'd fill her head with fear and bullcrap.