He never develops. Ever.
What was funny in a guy in his twenties just seems cringey in a man in his forties. He's a great big self-involved man baby. He overdramatizes everything and makes it about him.
He's just stuck in a massive rut as a character, and I don't think he'll ever change, because the show writers seem to think there's something funny and appealing about it. I got sick of him a long time ago.