It seems that you folks have more of a problem with Kay's "harping" than Michael does .

When Michael asks Kay to marry him, he makes it a point of trust to tell her that the family business will be legitimate in five years. I think it's a goal he aspired to as well. In light of the proposal, his uttering that statement to her has the implication of a vow, a promise, made especially for her. In fact, it was the one confidence regarding his business that he would share with her. Therefore, Kay has every right to ask about it.

And Michael's actions denote that even he believes she deserves that right. When she broaches the subject at Anthony's party, his reaction is not to snap at her, or to reply with stony silence, but to answer her gently with, "I'm trying." The voice is resigned, as if expecting this moment when he would be called to account; and it's also somewhat rueful: he knows he has disappointed both her and himself.

I think someone once wrote on these boards that Kay was Michael's conscience. Other times Michael can rationalize and fool himself into believing that he has already achieved legitimacy. But when confronted with Kay's simple, direct questions, he has difficulty preserving that illusion. Maybe Michael needs -- even welcomes -- Kay's prodding, just as a dreamer needs a pinch -- that small kernel of discomfort -- to prove that he or she is awake and back in reality.

BTW, we only see Kay remind Michael of his legitimacy plan once in seven years. If a guy has a wife who nags him only once every seven years, I bet he considers her a real find .