@purple_bobby I know that feeling! I've been around since DOS vs CPM too, and I'm still reading Dilbert at work, so I've probably made a similar series of wrong choices. :) I have a colleague in the same boat who calls it his "success avoidance mechanism".
Dilbert was being facetious in the second panel. To anyone with a modicum of a functioning brain it would have meant no, but this moron doesn't get it and still has to ask "So...yes?" Meaning "Do you still want my help then." Common case in people who do not understand indirect negative responses.
May be if the choices were binary (black and white).
I would partly agree with LeadPal: removing one choice might make it easier to choice among the remaining, assuming it was worth the time listening people like him.
I do seem to be consistently good a choosing the wrong future technology: Transputer over the ARM, CP/M over MSDOS, Objective-C over C , client-side Java over server-side ?, giving up on Java over not, Symbian over Android...