Problem Secretary

Problem Secretary, Phillip Andrade’s free quirky serif display font from 1999, has the offbeat, literary air of old office ephemera seen through a slightly surreal lens. The letters mix tall, reaching forms with soft, rounded curves and spiky little feet, so the alphabet feels formal at first glance, then pleasantly wrong in a way that keeps it lively.

That makes this free font a natural fit for book covers, poster titles, zine mastheads, café menus, packaging, and short editorial pull lines where a hint of oddity helps. It also works well for title cards and monograms, because the caps and lowercase both have enough character to carry a few words on their own.