WOW: Adolescent. Bobby Singer's relationship with John Winchester was a tumultuous one, and although Bobby may have sympathised with John's choices, he didn't have to like or approve of them. Through it all, one thing that never wavered was Bobby's love for John's boys.
A pre-series timestamp in two drabbles based on Dean's comment in 1.22 'Devil's Trap', so maybe teeny weeny spoilers for that episode.
Disclaimer: I don't own them, but then they're traumatised enough.
Two boys sat silently on Bobby's couch watching cartoons
Sam, a painfully shy eight-year-old was withdrawn to the point of being sullen, and Bobby knew from experience he could be defiant and wilful.
He watched the little shrimp clinging to his brother, the only person he trusted.
Of course the kid was a handful; he was rootless, confused and unhappy. Bobby could relate, and his heart bled for the boy.
He didn't want to be around the Winchester household when that kid hit adolescence. John Winchester had set himself up for a heap of trouble.
And the bull-headed idjit deserved it.