"Sounds like something rude to say. Or at least clueless in its hurtfulness."

Bingo! I think it was completely clueless and thoughtless. And the odd thing is that he thought it should make me realize what a grown-up he really is or is trying to become.

If he and I see each other during my break, then I think something light and quick would be best. Unless he quits his current job by the time my vacation starts, he'll be at work, and I'll be left to my own devices. [Insert gleeful laugh here.]