Never had any mathematical conversations with anybody, because there was nobody else in my field.
I tried reading Hilbert. Only his papers published in mathematical periodicals were available at the time. Anybody who has tried those knows they are very hard reading.
The only thing that might have annoyed some mathematicians was the presumption of assuming that maybe the axiom of choice could fail, and that we should look into contrary assumptions.
I was an undergraduate at Princeton, and I was pressed by the math department to go on to graduate school. Actually they gave me fellowships that paid my way, otherwise I would not have been able to continue.
Well it was not exactly a dissertation in logic, at least not the kind of logic you would find in Whitehead and Russell's Principia Mathematica for instance. It looked more like mathematics; no formalized language was used.