I agree with Indrius!! Dilbert can't find a woman who can stand his presence for ten consecutive minutes and yet when he finds one that actually likes him... yeah, he's never gonna mate.
I can see both sides...in the second...and third...frames...this is the sort of thing that I'd rather not be the fly on the wall for. Did she ever get that elbow rub?
LOL! I saw it completely the opposite. Buying someone shirts, IMO, is pretty clingy and creepy to do after one date. I interpreted this as an unusual turn of events where, for once, Dilbert was the normal one.