I was feeling sad, so I began drawing to help me feel better. Fluttershy's age thingy just happened to be among the substantial amount of arts I drew, so here she is.
As I said, I really didn't do much with Rainbow Dash's age thingy in terms of headcanon, but because her past ties closely with Fluttershy's I'll just kinda do that both here.
Baby Foal (Age 2-3 months):
A baby Fluttershy with her father, Sunburst. He's a canon, but very minor, background character and I thought he'd be a pretty cool fit for the dad of Shy, so I chose him. Of course, because he doesn't have much of a backstory so what I say about him here is all headcanon.
So, for me, Sunburst is a average sized stallion with a large heart and even larger soul. He's brave, self-sacrificing, and loves to help others. It's why he took up his dream career of being a firefighter. He was originally going to be a soldier, but I figured firefighters and law enforcers really don't get the credit they deserve, so firefighter he is. :3
The scars he harbors are from the job, but exactly how he got each of them is another story all on its own.
So, here he is with baby Fluttershy, the both of them taking a nap. Well... uh... Sunburst's taking a nap, anyway. Fluttershy was supposed to do so, but her tired father dozed off before she did, and she's wide awake. Now she's simply staring up at him, curiously looking at the scars adorning his face. The way I see it, Sun would be a wonderful and loving father, the type who'd join a tea-party at his daughter's request, and Shy would be a bit of a Daddy's Girl. c:
Knowing Fluttershy and Rainbow Dash were childhood friends, I have the headcanon that they met way earlier than in flight school. With their parents being good friends with one another, they were bound to meet, and here they are about 2 years after being introduced to each other. (Rainbow's about a year older than Shy)
From the day they met to the present, they will be the best of friends, so close to the point that they'd be sisters in all but blood. So here they are, being adorable and such, with RD giving an affectionate headbump to little Shy-Shy. c:
(while I think they'd make a cute couple, these two are among my top BROTP o3o )
It's mentioned and shown in the canon that poor Fluttershy was a target to quite a bit of bullying. RD too, if I'm remembering right, but I think it was more implied than anything.
Poor Fluttershy has been bullied for a good portion of her life, mostly because she was smaller-than-normal pegasus and some even exploited the fact that her mother was an earth pony (despite different-breed couples being the norm). The worst of the bullies would call her "mutt" or "halfbreed", and since she had more of her mother's affinity for the ground, they referred to her as the "fake pegasus".
It got pretty bad a little after her father died saving the lives of others when a business building caught fire. She became far more reserved than she usually was, and only her mother, and Rainbow's family could make her smile. The bullies didn't know why she withdrew more, but all they saw was an easier target. Some of them backed off and left Shy alone, but not all (the main offenders being the ones we see in the canon show).
Rainbow Dash was bullied as well, but not to the extent Fluttershy was. Dash was always protective of the younger filly and defended her, but it really came to a hit after Sunburst's death. So much as an ill-willed word toward Fluttershy would ignite Dash's anger and she'd immediately put the bully in their place, sometimes going so far as to get into an all-out fight. A lot of the time she was too much of a scrapper for anyone to actually handle in a fight and they'd get the hint, but every now and then it'd get bad before the teachers could put a stop to it.
This is one of those instances, with Fluttershy trying her best to tend to Rainbow's cuts and bruises before they go home. Despite Rainbow's insistence they tell their parents about it, Fluttershy would beg her friend not to and eventually made her swear not to tell; she didn't want to trouble her mother anymore than she was with the recent loss. This went on for a while before a concerned teacher caught the bullies in the act of harassing the two, and made the call to their parents. They managed to put a stop to the bullying and put their daughters minds at better ease, but they eventually make a simultaneous move to Ponyville.
Fluttershy all grown up to how we know her in the present. The way I see her, she's a bit taller than the average height of a mare, long wings (with a very impressive wingspan; her wings are more meant for long-term gliding and climbing, not so much speed), a slender body and long legs; I kinda wanted her to have an almost deer-like stature, to the point that some ponies even compare her to the body type of an alicorn. She also has the longest mane and tail of the Mane 6... guys. I love Fluttershy's hair, man. ;_;
Like her mother, Fluttershy has a decent-size magic font and is very skilled at healing and growing types of magic. Most of said magic reside within her hooves and the tip of her wings.
Like I said earlier, Shy-Shy will eventually become involved more often with political and royal affairs, where she will be named a "Knight of Equestria" and known to be very persuasive based on her disposition alone. If that doesn't work, then she certainly has The Stare in case things get hairy. She'll eventually become a renowned healer and animal/creature tamer, too.
Soooooo yeah. That's all I have for this one for now, I think. Two more to go! And maybe a few other characters as well; we'll see. Anyway, feel free to ask if you have a question or perhaps share your own headcanon. As always, thanks for stopping by to take a look. ^.^