My favorite fonts used to be Caxton and Cabaret. And I once used the former, paired with Impact, to typeset (using the term loosely) the bylaws of an Armenian youth organization I was a member of.

In my defense: I've had a bad vibe about Helvetica since day one.

hhp

In that case, I should probably «admit» I've never really hated Helvetica.
But perhaps it's also kind of hard to do that growing up in Switzerland. :)

My first favorite font, which I loved dearly, was Bookman. I used it for school papers, which was probably fine until I started pairing it with something like Blur for titles and subheads. Nobody could read it, but I tried very hard to ignore those comments because I just thought it looked so very cool. :-)

I once used Hobo for the logo of a lawn care company (just one guy really, a friend). He was pleased with it. In my defense, this was the late 80s. But Hobo was probably already dated/overused.

Hm... Well, I like to I think I had relatively good taste in type even when I was in high school. The earliest typefaces I remember liking back then were Windsor, Avant Garde, and Bookman, all in rub-down type. I remember thinking the ITC faces I saw in the Chartpak catalog were the best-looking. I had an aversion to what we call "retro" now--brush scripts and the like. I used Korinna for my first personal letterhead when I was in college in about 1975. I think my wardrobe was more cringe-worthy than my type choices back then--polyester shirts, bell-bottoms, and aviator frames. Bleah.

Back the the 90s I turned in a college English paper typeset in Arial. The professor was not happy.

In 1961, as my high school yearbook editor, I used Clarendon bold italic for major heads with the body text in Craw Modern.

ChrisL

I feel sincerely sorry for my middle school yearbook cover design. I had combined a playful brushy font with Copperplate, the latter set in a rainbow of colours, which was cringe-worthy enough. But the yearbook advisor was attached to the idea of using Aboriginal paintings—the kind with colourful mosaic-like arrays of dots—for the background, which left the cover an undistinguishable splash of various colours and rendered the whole thing unreadable. Even my young self knew that the type and cover didn't go together, although I dared not speak up about it.