In Plucky Pennywhistle's Magical Menagerie, Dean bonds with a little boy, as he has been known to do. But the way Dean bonds with this particular boy strikes me as skeevy.
The bonding starts when Tyler is pissed that a kid is cheating at one of the games. Dean uses his adult status to chase off the boy that was cheating, and he and Tyler bond by calling the kid a “jackass”. Dean, being the petty asshole that he is, proceeds to take the tickets that had been left by the cheating boy behind Tyler’s back. This is not a good start to the relationship.
Dean then observes Tyler with his mother, and starts trying to convince Tyler that Tyler should make life easier for his mother. Explicitly, he identifies himself with Tyler. “I've been where you are.[…]my dad, he... hauled me places.”
Dean uses his status as the “cool adult” to convince Tyler to be more sympathetic to the uncool adult (i.e., Tyler's mother). One thing that makes Dean a “cool” adult is that he totally agree with Tyler’s assessment of the pizza: it’s “butt”.
But there’s a con going on here. Not only is their original bonding a con, but Dean telling Tyler he identifies with him is a con. That is - it’s true. Dean was in comparable situations as a kid, many times. In a way, being forced to watch Sam when he would rather be “trolling for chicks” was one of those situations.
But he also identifies with the mom. Someone online once pointed out that Dean’s actually being super unfair to himself here. He was a kid, not a mom. Sam was not his child. Sam was their father’s child, not Dean's child. And Dean was exhausted not just from watching Sam, but from having to provide age-inappropriate emotional support to his very adult father.
But nonetheless, Sam's complaints earlier are foremost on Dean's mind, and he is identifying with Mom. She’s working hard to take do her job and take care of Tyler. Just like Dean - and just like John, who in young Dean's eyes worked hard to protect the world, raise his sons, and avenge his wife.
So in a way, in defending Tyler's mother to Tyler, he is also talking to Sam about Dad. Dean wasn’t really the kid who took his father’s emotions insufficiently into account when making decisions. Dean’s not really telling his past self, treat the adults better. This is crap that he told himself when he was his past self - not stuff he needed to hear from someone else (I don't think John told Dean to take emotional responsibility for his family, I think he just put Dean in a lot of situations where no one else was doing it). No, he’s talking to Sam. In more ways than one. Make Dad’s life easier, and make my life easier. Make the family’s life easier.
It’s interesting that Dean does not attempt to communicate any of this to Sam this episode. He doesn’t say, you know what, I took care of Dad and I took care of you and I hunted and I did everything I was supposed to do, and it wasn't fair to you, but sometimes I wanted a break.
Tyler listens to Dean, and dutifully puts aside his emotional needs when his mother is too tired to deal. Tyler thinks Dean was identifying with him, and that's the lie. Because Dean was identifying primarily with Tyler's mother. His treatment of Tyler is a dishonest manipulation from start to finish.