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safe2281438 derpibooru import1690071 edit173039 edited screencap86277 screencap295108 applejack213994 fluttershy276328 pinkie pie273432 rainbow dash298752 rarity232050 twilight sparkle376834 human236610 pikachu1038 ash ketchum157 best human170 best ponies13 bravery184 bulbasaur118 charmander115 clothes679497 compassion382 courage388 crossover73461 cute266382 dashabetes13070 diapinkes12321 group hug1287 heartwarming1836 honour190 hope266 hug39384 if only399 integrity172 jackabetes7878 kindness621 loyalty375 mane six39550 optimism166 perseverance96 pidgeotto9 pokémon11300 primal351 raribetes6842 shirt44954 shyabetes19123 squirtle89 t-shirt7806 twiabetes14560

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Anonymous #BB02
In my headcannon, Ash befriends Rainbow first. Fitting since they’re sassy yet sweet. And Flurtershy be second. Fits they be pals due to being animal carers.
Pinkie. Zero shock. Jolliness.
Ash with Applejack. Zeor shock> Spunk.
Rarity. It be grand if Ash try to calm Rarity when she overreact. And act as her conscience whenever she hurt Sweetiebelle.
Twylight. It rock if Ash help Twylight redeem herself for her sins. He’s capable of mercy such as forigivng Mewtwo even after his past errors, and also to Molyl evne after her errors.