Tony was not under the impression he had the ability to make anyone feel better about themselves, or that he had much patience, so it still wasn't clear to him what had changed how Tommy was treating him until Tommy suggested the Calibrations. Because they had fun together, was Tony fun now? Was that all it took to override what he did to piss Tommy off so much? He would figure it out eventually.

As much as Tony did appreciate Tommy not immediately chewing him out, on this reflection, he didn't appreciate how much Tommy seemed to be aware of and have opinions on his personal life. Especially without some apparently crucial context, because he had to ask, "Cap...?," not sure who else Judgmental Asshole could be in this tale Tommy had constructed.