You told him to stop and he did. Previously you ignored his comments so how would he know to stop? Or made comments like “whatever”, which again is not asking him to stop.

When you shared that story before I misunderstood that he kept doing it after you asked. But that’s not the case at all. See you said before that you want people to be honest and direct and tell you exactly what they think and you don’t want them to be people pleasers.

Yet you did exactly that. You kept going there suffering because of his comments yet never telling him to stop. So you were not direct and honest and expected him to read your mind, exactly what those “people pleasers” do.

Now you could say as a professional he should know better. But maybe he thought it’s just a silly banter to follow up your story. You shared about being drunk and kicked out of bars, was he supposed to lecture you on alcohol abuse? He thought you two are just doing friendly banter in a joking manner. He possibly thought you might like these jokes. How was he supposed to know.

All you had to do is to tell him to stop, which you finally did.