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When I inherited my Sweet Stuff and Sky Rocket from a cousin, they both came to me with cropped manes and tails I think the combination of the pose and haircuts made me think of them as boys. I also had quite a few babies that I decided were boys, like Splash and Stargaze. I always though it was a bit sad that the boys were so vastly outnumbered (heck, I still feel sad about that!).
For me Gypsy was my boy pony (I named him Max). I think because (as far as I remember) most of my ponies were white or lightly coloured so I made the darkest coloured pony male. He was always trying to win Majesty's favour by going on quests to get the hand (hoof?) of her daughter Starshine
When I was little I played with my cousin's Gusty and she was always a HE. I know she was a girl in the show and she was kind of a mean girl to say the least. When I played with my sister's Gusty he was such a sweet boy. :3 I need to draw male Gusty.....Dunno why I saw Gusty as a boy but I did...