Meet the Grayscales — run by sisters Derpy Hooves and Amelia Airhoof. I've featured Amelia's family before (you can see the other image I made with her at the bottom of this description).
In all honesty, I wanted to really stretch reality here and make families for many ponies who otherwise didn't have one in the show.
Here's who all is featured:
_ Amelia & Burnt Oak's Family → Dumbbell (their oldest son who studied outside of Ponyville to become a stronger flier), Silver Spoon (their second child and only daughter — hence why she was a little more spoiled than her brothers), & Chip Cutter (their youngest son)
_ Derpy & Time Turner's Family → Amethyst Star (their eldest daughter — she was adopted by Time Turner once Derpy married him), Crackle Pop (their second child and only son), & Dinky Doo (their youngest daughter)
I loved drawing all of them and giving the kiddos a family! Let me know what you think (but please be kind — this is just a head canon. No need to yell and scream about how you don't see one character with another)
Here's the other image I made featuring Amelia Airhoof's family →