Tough crowd over here at the CO forum.
Myself I think that any sincere chit chat which causes the GA to consider you as a person rather than just a record is fair. Over on the UA forum we call this "The Speach".
If your story is true, a dozen trips to the continent a year, ofter enough to be recognized on sight by the staff. . . one would hope an occasional op-up on a less than full full flight would require neither over the line flirting or much of a speach.
Look at it another way, if Y was oversold, SOMEBODY was going to get op-uped. Why not you? Good things come to those who ask - not as the old saying goes to those who wait!
Lihu'e 1k