It was your mistake for asking the either of them to come with you to school. You got in trouble and the principal asked a legal guardian to come to school.

"I don't want to deal with whiny people, take Sam." Dean said, dismissing you, but when you were about to turn to Sam, you heard him speak.

"You're going with her, maybe you'll get her out of trouble if you flirt with the principal." Sam was basically just mocking Dean.

This would be a nightmare.