Somebody better tell Flurry that’s his sister pretty quick, or Pumpkin’s head might roll!
 
EDIT 9/3/16: Added a link to Flurry Heart’s Cutie Mark. :) Changed Flurry Heart’s description a bit.
 
I don’t think there’s such a thing as liking Fairy Tail too much, or shipping Heart Pound too much!~ Love But does anyone else think there’s something unsettling about Pumpkin’s design? I did sketch her kind of quickly. And btw, those are giant cartoonish tears coming out of Flurry’s eyes. Anyway, here’s my headcanon:
 
Flurry Heart: She’s pretty much a spaz, though she is generally very good at completing her princess duties (MOM’S ASSISTANT/WORK HORSE IRL) and is a very nice, but somewhat superstitious pony because she listens to her mother talk about love and life so much. She just so happens to be a closet romantic. At least, her subjects don’t know how invested in love she is. When she is in love she cannot be reasoned with. Her mother is completely accepting of anyone Flurry loves, provided she actually HAS a special somepony, because Flurry Heart suffers from a social anxiety that only rears its head when she’s trying to talk to the stallion she likes. So she eventually regresses into simply stalking her crushes. Her father is a lot more touchy on the subject of Flurry Heart’s dating options. But they would be hypocritical to place Flurry in an arranged marriage to a foreign prince, specifically a Yakyakistani prince. (They’re actually considering it, but sshh, don’t tell Flurry.) Mostly Flurry Heart would like to be left alone on her terms; Basically she has mental tunnel vision. Also important, Flurry did grow into her wings and horn. She has her mother’s body type.
 
Flurry Heart can interact like a normal pony around Pound Cake even though she likes him because he’s on her personal Guard, so she makes the effort to be his friend first. Interacting with Pumpkin on a daily basis also helps. Age: 24.  
Cutie Mark (Credit to YupinaPegasus for designing a gorgeous Flurry Heart Cutie Mark before I could!)
 
Pound Cake: Pound Cake is a high-energy stallion. He became involved in Twilight’s Royal Guard early on in his life and received his Cutie Mark. Twilight has refrained from telling him that the wing on his flank has the colors of Flurry Heart’s wing’s gradients. He really liked working and baking in his parents’ bakery growing up.
 
He has worked in many different cities guarding various princesses, but he has only recently been transferred to the Crystal Empire to partake in Princess Flurry Heart’s Guard. (She doesn’t get out much. ;) (Wink) ) So when Pound Cake shows up for duty, specifically to help in guard training, Flurry Heart starts going insane inside because HE’S JUST SO PRETTY. She stalks him to the train station after a few days (BECUZ SHE’S A FRIGGIN’ ALICORN PRINCESS AND SHE CAN TAKE A BREAK), wondering why he’s there, and then she just assumes that orange mare that gets off the train and throws her hooves around him (WUT A WHORSE) is his friggin’ girlfriend. But no, Pumpkin is not, as Flurry soon finds out, but to keep her pride she somehow decides to play dumb and annoy Pumpkin further. Pound Cake never realizes this conflict between Flurry and Pumpkin and assumes they get along fine.
 
Pound Cake, as a character in my opinion, would always try to see the good in others, to the point of being taken advantage of. He sees Flurry Heart as a Princess that he’s guarding because he respects her, so he doesn’t notice the amount of shenanigans that Flurry Heart goes through to try to get his intention.
 
As for his hair, he let it grow out in the front because he thinks it looks cool when he’s flying. (Pumpkin happens to disagree rather monotonously. Flurry just squeals.) Age: 26.  
Cutie Mark
 
Pumpkin Cake: Pumpkin Cake is the more subdued of the twins. She is an accomplished magician and has graduated from Celestia’s School for Gifted Unicorns (NERD with a braid), and has been selected to be privately trained by Sunburst, who by this time has become a much more accomplished magician as Flurry Heart’s mentor. Her special talent ironically lies in baking and decorating pumpkin cakes and pies, in the magical way.
 
She and Flurry Heart don’t like each other much; Pumpkin was weirded out when Flurry accused her of being Pound Cake’s girlfriend (I MEAN WUT), while Flurry Heart can’t stand feeling like she has to compete against a second student of Sunburst’s. Starlight, who has married Sunburst by this time and lives in the Crystal Empire with him, shows up every so often to mediate cat fights. Starlight works in the Diplomacy Department of the Crystalian Empirical government.
 
Also, Cream is Pumpkin’s bestie back in Ponyville. Growing up, they had a lot of fun together running the Cakes’ shop. Pumpkin and Pound didn’t get along as kids, but they’ve matured and get along splendidly as adults. Age: 26  
Cutie Mark
 
Cream, Pound, and Pumpkin were nicknamed the New Crusaders growing up, but they were never involved in the actual creation of the modern Cutie Mark Crusaders/Filly and Colt Scouts run by Sweetie Belle, Apple Bloom, and Scootaloo b/c the notion hadn’t been conceived until the girls were adults.
 
If you don’t know who Cream is, well, she’s the purple haired foal from…“Mysterious Mare-Do-Well” I think? Look her up. :)