I guess I'm just real old school. That is the main aspect flavoring my perception of this.
There are just some things a true gentleman never says to a woman, and it is absolutely unthinkable to an older woman . . . . even if the woman does kind of set herself up for it. Just being a woman demands a certain amount of respect from men, and especially so from a younger man. I thought the guy was out of line, personally. But . . . that is just me.
Just the way I was raised, I guess.