It's a tragedy really, how Dean bonds so effortlessly with people who have shouldered the burden of parenting.
DEAN: You know, I gotta say, you did a bang up job with those two.
TASHA: You must be drunk. [...] Yeah. I did the best I could for Max and Alicia.
DEAN: No.
TASHA: I got lucky.
DEAN: I see how you are with them, all right?
12x20
Dean has to tell this woman. I SEE you. I SEE how hard you've worked. You are appreciated, you've done a GOOD job.
Dean's struggle is so often invisible too.
And yeah, Dean WAS A KID. But it was still a struggle that, as I've said ad nauseum, tends to get pathologized “Tangled up unhealthy thing," and fetishized (SEE: all of the incomparable Zachariah).
But no matter how unfair it was to live with, Dean needs his struggles to be seen for what they truly are. Fellow parents are more likely to see that, especially if they've been through the school of hard knocks and familial loss. Some people, like Ellen for example, see it so effortlessly , but others just... don't.
Like here, it doesn't occur to Tasha that Dean could be speaking from experience here having parented his own brother. She instead, gives him some advice about relating to his own parents. Not being one.
And yes, Tasha's words ignite sympathy in Dean re: Mary's struggles.
TASHA: Yeah. Family's always complicated. Parents always seem smart and strong and perfect. It's only when you grow up that you realize that they're just people. (12x20)
But Dean isn't often seen. We'll find him a couple episodes AFTER this... begging Mary to SEE him.
It also make us think about Dean's relationship to Bobby (SEE: Weekend at Bobby's) and ofc Sam's extended arc of seeing Dean in a more adjusted light:
SAM: No, the Dean I know... the Dean who raised me – he'd never give up, no matter how bad things got. (15x09)