Family picture! (just to clarify, I simply didn’t include berry because they don’t live in the same household, he’s not any less part of the family, though he’s indeed closer to his dad’s side)
 
I’d like to say I chose to give Cheerilee a bit of a stronger and rougher earth pony build. She’s fairly taller than the average mare, and is pretty strong for one. She needs to be ocasionally able to press a misbehaving stupid teenager or two to the ground when they refuse to go to detention lol.
 
On the other hand, Clear skies is petite~ Wind Sprint grows up to be a little taller than her because of her dad’s genes.
 
Rosemary is a slight mix of Cheerilee’s built and Clear Skies’ small figure~
 
As a way of going deeper into her background story, I’ll go a bit into how Rosie’s mothers came to be <3
 
Clear Skies is probably from somewhere in manehatten, or at least used to live there for a couple of years. Clear’s occupation revolves around cleaning, organizing and optimizing environments so ponies can make the best use of it, which was a job very frequently called for in the big city of manehatten. Everypony had their own rushed and busy schedules they didn’t have time to organize their houses or working spaces, to the point that it would affect their productivity and quality of life. Clear was there to solve that problem.
 
It was a couple of years after her husband passed away that she considered dating someone again, tho she didn’t really focus on it, and wanted to spend time with her daughter the most. Even so, a couple of relationships with one or another stallion would eventually come and go, but none of it really seemed to work out. Realising the big city wasn’t really a friendly and enjoyable place for a single mom and a little kid to live, Clear Skies decided to move to ponyville with her daughter Wind Sprint. Ponyville was a very lively and peaceful small town that had a much bigger feeling of community. Much more contact with nature as well as better place for Wind to enjoy her passion for sports, also knowing ponyville was where one of the best teams of hoofball resided.
 
Since ponyville is a much more quiet and simpler place than the big city of manehatten, Clear Skies’ former job wasn’t really much requested. She’d often help out older ladies cleaning up their houses and give the grocery shopping employees a hand on organizing the shelves. But she was used to the rush of the big city, so she couldn’t really spend much time sitting still. As a way of also focusing on her daughter and being around while she grows, Clear Skies decided to be a volunteer for the Ponyville’s Schoolhouse. There she would meet Cheerilee, who she’d spent a lot of time with, since the teacher was responsible for overseeing all sorts of school events, specially for the youngeer fillies. Clear Skies would help with class organization, planning family meetings, events, and sports festivals. They would bond over their love for younger children, both being single moms (since at that time, little Mulberry was around the age of a little colt too). Eventually things just flowed naturally from there. Clear would grow closer and closer to the mare, not realizing her feelings for a while. Cheerilee was the first one to confess as she had realized her feelings first. Clear Skies was confused as she never really felt anything or had even considered a relationship with a mare. But they eventually sorted it out and live happily together now~
 
Now have some random family relationship notes!
 

 
Also, just to clarify, the Ponyville Schoolhouse Cheerilee used to work in has been upgraded over the years and have become a much bigger educational facility. Cheerilee’s performance over the years has earned her lifelong dream of being nominated school principal~
 
Anyway hope you like it! Don’t worry there’s still more to come