#and i think a lot of his “positive encouraging feedback” to arthur also contains barbs

[divinekangaroo]

"running joke about Tommy’s invariably double edged compliment-giving skills"

explain!?

...so in S4, there's a scene between Tommy and Lizzie where Lizzie tells him the office girls are hiring a prostitute to deflower Young Finn, and Tommy tells Lizzie to get some more cash and upgrade the tier of prostitute engaged so Finn "has a nice one". Paraphrasing from memory (this is not exact), part of the exchange goes like this:

Tommy: ---make sure you get a nice one

Lizzie: girls who do this sort of thing aren't nice

Tommy: (goes oddly demure, oddly flirty, abashed, bats his lashes) you're nice

Lizzie: (pulls one of her wildly complicated gamut of emotion confusing faces)

in my head, I was imagining her thinking something like the below where all thoughts occur simultaneously:

/ did...Tommy just give me a compliment? did he say something nice? to me? about me? what does he want from me? is this starting up again? / did...Tommy just deliberately remind me [I am] [I was] a prostitute again? / did he just fucking put me back in my place for expressing an opinion in an area where *I* actually know more than he does? / did he just....step completely out of line with me by bringing this up about me again, if, say, for example, I happened to even *have* any lines with this man? did he just cross my non-existent boundary?!?! why do i have no boundaries?? why does everything he says remind me I have no goddamned boundaries!! / did, did, did Tommy just suggest that *i* should be the one who............./..........OMG i can't believe that for a fraction of a second I thought Tommy just suggested *I* should deflower his little brother.... /

From which I have spawned an entire running headcanon that no matter what compliment Tommy gives any person alive, even if intended benignly, sincerely and motivated by kindness and fondness and care, it will spontaneously generate a spiral of pleasure/confusion/shock/doubt/hurt (and occasionally horror) in whoever receives the compliment, either because:

he somehow always manages to land on a combination of words and context that goes around hitting everyone's sore spots (because his way of living often means his overlaps/interactions with people involve sensitive actions and activities -> eg here he probably did just think "you're nice and you were a prostitute, that's ok?" but because it's such a complex, disempowered time of life for Lizzie, of course it's gonna hurt him putting her back into that frame even if he doesn't realise)

they have an image of him in their head [that isn't him] and they'll misread/add frames to fit that image of him, that make him seem more cutting, smartarsed and sharp than he actually intended