One of my favorites was a guy who, working through a sales rep, kept asking for a “fun font”. We didn’t have too many, um, “fun fonts” on stock, so we did what we thought was best. Guy literally came back with, that one sucks, try again. Honestly, his exact words.
We tried another. No.
Another round of revisions. He questioned whether we have a mental handicap (not his exact words.)
So he sat down at his own computer, looked through his list of fonts, and zeroed in on…
Arial.
And of course, because we all had a screen-only version of Arial on hand, we used Helvetica instead.
Helvetica. The “Fun Font”.
EDIT: I should mention: this guy was a real-estate agent. This was the same font we used on all his ads.