Not really. Dick got talk texting cringe pickup lines even a teenager would consider awkward to a 35 year old woman while also offering to give her money. When it leaked, his internet friends acted super defensively and called him an uberchad. If DMs of Mundane Matt had come out with him telling a married woman "i'll buy you wings, angel" he would be raked over the coals for a week straight and Ralph would be selling tshirts, but it's Dick so we're supposed to pretend that not only are they not hilarious, they're actually extremely alpha.
In truth the extreme reaction is a culmination of a sense that has been building for a while, that the Killstream and its peripheral members are hugely thin-skinned unfunny hypocrites and maintain their hugbox with manufactured safe-for-work drama. They built the Killstream on a skeptic burial ground and through some Sargonic curse are beginning to more and more resemble the same cliquish incestual faggot-filled community they once maligned.
Also Dick Masterson flagging down videos laughing at him was a bad look, but no one seems to push that point for some reason, probably because Jesse's an f-slur.