seems like lots of people have sand in their vaginas here.
Personally, I'd start out with some "sure thing" wines - that is, ones that are highly prized worldwide and cater to the palate of most semi-serious wine drinkers/collectors: I'm talking about the first growths from Bordeaux, some right bank Bordeaux (Ausone, Cheval Blanc, Lafleur), some Italian Piedmont (Gaja), some Tuscan varietals (Biondi, Ornellaia, Sassicaia), champagne, port, and then some white burgundy and some red burgundy (DRC, Leroy, etc.).
If he doesn't like any of these wines, no big deal. He could flip them in a year or two and probably make a profit. Plus, finding these wines isn't easy (try winebid.com for the tough stuff) so if you can assemble a respectable collection, it shows much more thought than just handing over money.
And please, this is not analogous to just buying somebody a suit. I'm a wine and suit lover, and I'd absolutely hate it if somebody bought me a suit - but I'd love some nice bottles of wine no matter what country they came from or what varietal they are.