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Background Pony #81D9
@ShimmeringStallion  
You make an excellent point, and I think it would actually be funny if they ever did an episode one day about Dash meeting her childhood bullies, and it turned out that was (at least somewhat) the reason behind what they did. Heck, if the toys are any indication (or the advertisements for them at least) they’re starting to consider the younger male demographic more anyway, so that could be a good lesson for some younger boys to learn.
Background Pony #81D9
I ship it, it’s ironic and sexy.
I can’t help but feel that it would be kind of an unusual pairing, considering their past history. But then this is Rainbow Dash… the fandom has paired her up with far more bizarre ponies (and non-ponies, and non sapient life, and objects) before.
 
Alternatively, it turns out that he’s gay, and he reveals the reason he tormented her frequently when they were younger is because he was lashing out over feelings he couldn’t (or was afraid to) express. Although I get the feeling the artist was thinking something else here, obviously.