It would be lovely if you'd point that kind of thing out to the nerdy guy. One problem with being a nerdy guy is that a lack of romantic experience creates a positive feedback loop.

So yeah, it's great to point out what mistakes the guy made. See Epiphany's comment here.

(I have no doubt that you personally would do this, I'm just pointing this out for future reference. You might not remember, but I've actually talked to you about this positive feedback loop over IM before. I complimented you for doing something which would go towards breaking the cycle.)