Short version: I work with a guy in his mid-20s (I'm mid-30s, divorced, father, fairly successful and ridiculously happy).

Anyway, he's dating a girl in her early 30s and he's heading for a trap! She's moderately famous, somewhat successful and quite hot, and I'm afraid he's blinded by the illusion of status she gives him. He's very talented, ambitious, good looking, but most of all he has his whole life ahead of him! And he's crazy over this chick, and unsurprisingly she's started dropping baby hints like crazy.

I was young and in love once. Nobody could have talked me out it, and I see that in him now... but I do care about him. How do you go about chipping away at the delusion?