Jill, a 24-year-old with a love for fashion and all things glamorous, had always wanted to share her interests with her younger brother Derek who she suspected was gay. Derek, on the other hand, was a 20-year-old man who preferred comfortable jeans, sneakers, and minimal fuss when it came to his appearance. Despite their differences, Jill saw potential in Derek's appearance and decided it was time for a sisterly day out---one that Derek wouldn't forget.

One afternoon, Jill casually asked Derek if he'd like to go shopping. Derek hesitated, unsure if he really wanted to spend hours in clothing stores, but Jill's enthusiasm was infectious. "Come on, it'll be fun! We don't have to spend all day there," Jill promised with a bright smile. I'll treat dinner for your company. Reluctantly, Derek agreed, figuring it would at least be a good chance to spend some time with his sister.

They started at a small, trendy boutique. Jill led the way, carefully picking out a few items she thought might appeal to Derek. At first, she selected more neutral pieces---a soft, fitted hoodie, a pair of skinny jeans that flattered Derek's athletic build, and some sneakers with a subtle pattern.

"You know you might look cute in these," Jill told him. "It's just like the stuff you usually wear."

"They are girl's things."

"When we were kids, you let me dress you up all the time."

"I was four."

"You loved it!"

Derek tried them on, surprised at how good he looked in clothes that were a bit more fitted than his usual baggy attire.

Seeing the small spark of confidence in Derek's eyes, Jill decided to push the boundaries just a bit more. She handed Derek a floral sundress, something light and breezy but still casual. Derek hesitated, eyeing the dress as if it were an alien object.

"Try this, I was always curious what you would look like."