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In my headcanon, pegasus families are not very close, especially in Fluttershy's case. Her parents saw her as a disgrace because she could hardly fly. That's why, when she fell from Cloudsdale during the race, nopony ever came looking for her. She settled into a small cottage with her new animal friends and for a long time she let herself rot there. She felt alone, unwanted, and although she had her critters, she was very scared. It was only when Rarity happened to find her one morning, out looking for gems, that Fluttershy made her first pony friend since she lost Rainbow Dash.
Rarity grew up in a very liberal family, and she always found them extremely crude and obnoxious. She dealt with it as a filly, turning her attention more towards fashion and the arts. When Sweetie Belle was born, the Belle family fell into a financial crisis, and by that time Rarity was old enough to sell some of her designs. She developed a conservative demeanor, which was accompanied by a learned fake accent because she thought it was "civilized." She supported her younger sister in a way that she felt her parents couldn't, and although she has since opened up her own shop and moved out, she is still her family's greatest financial support. She secretly resents her parents and sister for inadvertently causing her to give up her childhood prematurely.
Rainbow Dash lives on the outskirts of Cloudsdale with her parents but, as mentioned above, pegasus families are not close, and so her parents are hardly ever home. In fact, some fillies and colts from pegasus families live on their own for weeks or more at a time... Even years! Her parents are never around, and the only reason they still let her live with them is because of her great athletic prowess, which is valued in pegsus society. She turns to her friends for the love and support she lacks at home, but she can't admit that to them, for fear that they'll call her "soft." Consequently, she takes her pony friends under her wing, so to speak, and because of her insecurity will never leave them, hence her title as the Element of Loyalty. Separately, she always regretted her inability to leave Cloudsdale and search for Fluttershy, and eventually presumed she had died from the fall like everypony else believed. Imagine her face when they met back up at one of Pinkie's parties!
Applejack was never too close to her parents. They were always out on business, leaving her and her brother (Along with Granny Smith in her younger years) to care for the farm and the little filly Applebloom. They were in an accident on the train, but AJ never really cared, nor did Big Macintosh (At that point he was still known as Apple Macintosh). In fact, it had been a couple of weeks before they realized what happened. Applebloom never spent more than a few days at a time with her parents, and she can't remember them now.
Twilight Sparkle went to boarding school to study alongside other gifted unicorns when she was young, so she hardly ever spoke with her parents. When she did, it was during summers and holidays, but by that point, Celestia was her role model and mother-figure, and Twilight didn't click with her parents like she used to.
Pinkie grew up in a "rock farm," similar to a mine. After she discovered her super-special talent, both she and her family realized that this was not the place for her.Her family loved her very much, despite the overall gloominess of the farm, but they knew it was in her best interest to send her away. She went to live with her Granny Pie in Ponyville for a long time until her grandmother died peacefully in her sleep. Pinkie reverted to Pinkamena, an alternate personality due to her sudden change in demeanor, for months in mourning, until she moved into Sugarcube Corner with her aunt and uncle Cake. The cakes let her live there and pay her for her work in the kitchen, but most of her paycheck goes back to her family on the farm. They throw parties in her absence as a celebration of their beloved daughter and sister, and occasionally she will write a letter. The farm depresses her, though, so she rarely visits.
Rarity grew up in a very liberal family, and she always found them extremely crude and obnoxious. She dealt with it as a filly, turning her attention more towards fashion and the arts. When Sweetie Belle was born, the Belle family fell into a financial crisis, and by that time Rarity was old enough to sell some of her designs. She developed a conservative demeanor, which was accompanied by a learned fake accent because she thought it was "civilized." She supported her younger sister in a way that she felt her parents couldn't, and although she has since opened up her own shop and moved out, she is still her family's greatest financial support. She secretly resents her parents and sister for inadvertently causing her to give up her childhood prematurely.
Rainbow Dash lives on the outskirts of Cloudsdale with her parents but, as mentioned above, pegasus families are not close, and so her parents are hardly ever home. In fact, some fillies and colts from pegasus families live on their own for weeks or more at a time... Even years! Her parents are never around, and the only reason they still let her live with them is because of her great athletic prowess, which is valued in pegsus society. She turns to her friends for the love and support she lacks at home, but she can't admit that to them, for fear that they'll call her "soft." Consequently, she takes her pony friends under her wing, so to speak, and because of her insecurity will never leave them, hence her title as the Element of Loyalty. Separately, she always regretted her inability to leave Cloudsdale and search for Fluttershy, and eventually presumed she had died from the fall like everypony else believed. Imagine her face when they met back up at one of Pinkie's parties!
Applejack was never too close to her parents. They were always out on business, leaving her and her brother (Along with Granny Smith in her younger years) to care for the farm and the little filly Applebloom. They were in an accident on the train, but AJ never really cared, nor did Big Macintosh (At that point he was still known as Apple Macintosh). In fact, it had been a couple of weeks before they realized what happened. Applebloom never spent more than a few days at a time with her parents, and she can't remember them now.
Twilight Sparkle went to boarding school to study alongside other gifted unicorns when she was young, so she hardly ever spoke with her parents. When she did, it was during summers and holidays, but by that point, Celestia was her role model and mother-figure, and Twilight didn't click with her parents like she used to.
Pinkie grew up in a "rock farm," similar to a mine. After she discovered her super-special talent, both she and her family realized that this was not the place for her.Her family loved her very much, despite the overall gloominess of the farm, but they knew it was in her best interest to send her away. She went to live with her Granny Pie in Ponyville for a long time until her grandmother died peacefully in her sleep. Pinkie reverted to Pinkamena, an alternate personality due to her sudden change in demeanor, for months in mourning, until she moved into Sugarcube Corner with her aunt and uncle Cake. The cakes let her live there and pay her for her work in the kitchen, but most of her paycheck goes back to her family on the farm. They throw parties in her absence as a celebration of their beloved daughter and sister, and occasionally she will write a letter. The farm depresses her, though, so she rarely visits.
Don't judge! Headcanons are fun, even the stupid ones because they're funny, and these are mine. I don't actually believe them, but they're fun little background stories for the Mane 6. If you don't like them or think they're stupid, I'm very sorry and I'll take them down.
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I assumed that Flüttershy's parent's are finically well off and really care about protecting her. She doesn't seem to have much of a higher education and it looks like she's never done an honest days work in her life. Yet, she has the funds to attend a pricey spa every week, and make regular trips to the local farmer's market and pastry shop. She also live in a sweet-ass two story one bedroom cottage on a giant piece of property on the side of the Everfree Forest.
So, who's paying her. I can tell you it defiantly isn't they animals, because animals don't got much money. You might be able to make the argument that she is paid by the city to work on keeping the animals well off, but city employees don't make much money and that would have to mean that her cottage is owned by Ponyville which is impossible if you count Season Two as cannon (which I don't) because the cottage quickly falls into disrepair after she doesn't take care of it. If this happened with city property, the mayor would evict her before you can say 'Appleoosa'.
No, the only option is that she has rich parents that love her enough to respect her decision to not peruse a real career path or college, and instead fund her passion to live far away from them. Also; powerful phobias are a sign of smothering parenting. Her shyness implies that she is the youngest born of a (possibly large) family. So while she is favored by her parents, they have many more foals to deal with. They might find it convenient that she has moved on to be out of their manes.
But then, that brings up the issue of what gives them love, and why they don't constantly visit if they love her so much. The answer is very simple. They run a fairly successful family business that employes her brothers and sisters, so they always have children to be attached to. What is this business? Clothes design and manufacturing. This alternative pegasus life style explains why they would be excepting of Flüttershy's desire for a non traditional pegasus life. Aswell as why she has a "Creepy knowledge of sewing," as her knowledge of fashion. This also explains her desire to maintain relations with Rarity, a mare who she has nothing in common with, personality wise or career wise. Rarity reminds Flüttershy of home.
So, who's paying her. I can tell you it defiantly isn't they animals, because animals don't got much money. You might be able to make the argument that she is paid by the city to work on keeping the animals well off, but city employees don't make much money and that would have to mean that her cottage is owned by Ponyville which is impossible if you count Season Two as cannon (which I don't) because the cottage quickly falls into disrepair after she doesn't take care of it. If this happened with city property, the mayor would evict her before you can say 'Appleoosa'.
No, the only option is that she has rich parents that love her enough to respect her decision to not peruse a real career path or college, and instead fund her passion to live far away from them. Also; powerful phobias are a sign of smothering parenting. Her shyness implies that she is the youngest born of a (possibly large) family. So while she is favored by her parents, they have many more foals to deal with. They might find it convenient that she has moved on to be out of their manes.
But then, that brings up the issue of what gives them love, and why they don't constantly visit if they love her so much. The answer is very simple. They run a fairly successful family business that employes her brothers and sisters, so they always have children to be attached to. What is this business? Clothes design and manufacturing. This alternative pegasus life style explains why they would be excepting of Flüttershy's desire for a non traditional pegasus life. Aswell as why she has a "Creepy knowledge of sewing," as her knowledge of fashion. This also explains her desire to maintain relations with Rarity, a mare who she has nothing in common with, personality wise or career wise. Rarity reminds Flüttershy of home.