I've long suspected that Pintsize's off-colour humour, sexual harassment and apparent enabling of substance abuse is all just how he does his job of being Marten (and, increasingly, Faye's) friend, adviser, companion and, to a certain extent, keeper. He has found that his antisocial behaviour is the best way to motivate Marten to get out of his passive rut. He's also found that Faye will aggressively resist people telling her to not do something but that you can moderate her behaviour by walking the path beside her and listening to her vent.
I strongly suspect that the latter was his plan when Faye came home after being fired from CoD but she was so determined to seek oblivion (and possibly death, at least on a subconscious level), she shut him down to stop him from interfering. I also suspect that he was planning to use mockery to force Faye to admit to herself that her behaviour had been inappropriate, self-destructive and, fundamentally,
not what she wanted.
The problem Pintsize is having in today's strip is that it looks like Marten and Faye have moved beyond their previous personality paradigms. Marten has found a girl who is important enough to him that he doesn't need Pintsize to motivate him to be active in his relationship with her. Similarly, Faye has been sufficiently shaken by what happened to her that she is making a strong effort to change herself (hence the title of
strip 2889). Maybe he isn't needed anymore?
If I'm right, we may see this week a strip or two of Pintsize talking to Winslow about how to continue to help your charge when they are making real progress in changing their lives. After all, Hannelore is the most radically changed of all the characters in terms of how far she has made progress in facing her demons. Winslow probably has had to make lots of changes to how he carries out his duties to her.