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So basically in my headcanon, both Dumbbell and Gilda are dropouts from Equestria's education system. Gilda's family moved to Equestria to escape the increasingly impoverished kingdom Griffonstone, whos griffons were often victims of attacks from...well...other griffons. Groups from neighboring kingdoms who'd come to loot and pillage. Over time their people have reverted to the old ways. Griffonstone has in fact survived ten fires but those who still live there are poor as dirt. They stay due to some vexing sense of pride and a dead hope that rebuilding their home is possible. But the spiritual/communal foundations are not there, so nothing ever gets better. Gilda gets word that one of her family is sick and leaves Equestria two years before she would have graduated. And due to the desperate conditions of Griffonstone, she got stuck there.

Just a few months away from graduation, Dumbbell and Rainbow Dash get into a fight. The reasons are unknown but other students and staff remember seeing and hearing them clashing across the sky, and Rainbow Dash screaming that she wouldn't let some asshole bully hurt her friend ever again. The fight was so intense and caused so much property damage that the principal would have been mad not to expel the two. Though as it is with most things, they were allowed a second chance at redoing their final school year. Rainbow Dash didn't even feel like it, but her father wouldn't take no for an answer. So Dash eventually graduated becoming ,more or less, a productive member of society.

On the other hand, Dumbbell's entire attitude could be summed up as "fuck it". He hated school and he hated Cloudsdale so he left as soon as possible, already being of legal age, nopony could hold him back.

So some nondescript time later, these two find themselves together, young, inexperienced, and needing money, working the same job as airship freight workers. Transporting cargo all across Equestria, and even to places just outside it's borders, namely griffon country.

In this pic they could be talking about just about anything. Maybe even Rainbow Dash or what they remember from their school days. Or agreeing that their boss is a piece of crap who under pays them.

The little bobcat/owl griffon in the middle is just an OC I made. Her name is Gigi.

Description
So basically in my headcanon, both Dumbbell and Gilda are dropouts from Equestria's education system. Gilda's family moved to Equestria to escape the increasingly impoverished kingdom Griffonstone, whos griffons were often victims of attacks from...well...other griffons. Groups from neighboring kingdoms who'd come to loot and pillage. Over time their people have reverted to the old ways. Griffonstone has in fact survived ten fires but those who still live there are poor as dirt. They stay due to some vexing sense of pride and a dead hope that rebuilding their home is possible. But the spiritual/communal foundations are not there, so nothing ever gets better. Gilda gets word that one of her family is sick and leaves Equestria two years before she would have graduated. And due to the desperate conditions of Griffonstone, she got stuck there.

Just a few months away from graduation, Dumbbell and Rainbow Dash get into a fight. The reasons are unknown but other students and staff remember seeing and hearing them clashing across the sky, and Rainbow Dash screaming that she wouldn't let some asshole bully hurt her friend ever again. The fight was so intense and caused so much property damage that the principal would have been mad not to expel the two. Though as it is with most things, they were allowed a second chance at redoing their final school year. Rainbow Dash didn't even feel like it, but her father wouldn't take no for an answer. So Dash eventually graduated becoming ,more or less, a productive member of society.

On the other hand, Dumbbell's entire attitude could be summed up as "fuck it". He hated school and he hated Cloudsdale so he left as soon as possible, already being of legal age, nopony could hold him back.

So some nondescript time later, these two find themselves together, young, inexperienced, and needing money, working the same job as airship freight workers. Transporting cargo all across Equestria, and even to places just outside it's borders, namely griffon country.

In this pic they could be talking about just about anything. Maybe even Rainbow Dash or what they remember from their school days. Or agreeing that their boss is a piece of crap who under pays them.

The little bobcat/owl griffon in the middle is just an OC I made. Her name is Gigi.