Growing up
Winnie

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Your mom died when you were two, and you don't remember her. Your dad married Winnie's mom and adopted Winnie when you were both three years old. Coincidentally, she and you were born three hours apart but on different calendar days; your moms were friends and actually shared a hospital room. Later, as you grew up, you would joke about being twins from different mothers, and that's more or less how you grew up. You always regarded Winnie's mom as your own.
Winnie's mom died when you were both 10, and you were both devastated. After that, your dad raised the two of you alone. Winnie and you were inseparable.
After that, Winnie started acting like a tomboy. She wanted to be one of the boys. She was never interested in girly things, always wanting to hang out with you and your guy friends and play soccer and football and video games. She didn't even own a dress or skirt. Your father let her choose her own destiny, showering you both with love.
On your 1xth birthday, your father came back from Vegas with a new bride, a woman who is an icon in the fashion industry. You and Winnie were both shocked that he'd elope like this. But, despite your best efforts, you both quickly began to love your new step-mom, Andrea. It was good to have a mother-figure in your lives again.
But with her influence, Winnie started to change.