Masochist me/Clothes

From Create Your Own Story

I showed up to the training, wondering why we would need training for how to dress.

I knew how to dress.

"You," he said, point at me. Not like he had much option, as there was only three of us.

"I am forty year old client. I like younger girls, and we will be going to a high school reunion. What are you wearing?"

He pointed at a clothesrack, completely stuffed with clothes. Halter tops and tank tops. Capris and jeans. Miniskirts, long skirts, full length dresses and cocktail dresses. It had so many different styles that it was hard to decide what to wear.

Picks bad outfit, aiming for the young girl/old guy style

Instructor goes through, explains client would be at reunion, and aiming to impress his classmates

Instructor will guide me to a still young, but classy, outfit

Instructor will explain that client will respond better to a "trophy wife" look, rather than something else

Need more examples