I am in the process of organizing my riddle manuscript. I have decided to separate it into three parts since all my riddles seem to fall into roughly three categories:
1) riddles that most closely resemble the Exeter Book riddles both in content (vegetables, tools, minerals, weather) and form (kennings, formulaic)
2) riddles that describe objects of technology (cars, appliances atm) and/or a divide from the exeter book riddles (my animal riddles describe mainly dead or imprisoned animals while the exeter book mainly describes animals in the wild)
3) riddles about artifacts, encounters, or "existential" riddles that ask questions no one can really answer (i have many riddles about death, art objects, riddles about poetry itself)
While I am organizing my manuscript, I am also writing new poems to add to the collection (sorry Medrie!) Considering that Aldhelm wrote 100 riddles, Symphosius wrote 100 riddles, and the Exeter Book very likely contained 100 riddles, I am finding it impossible not to write 100 riddles. I also want to write a few extra to replace the ones that suck.
I recently took another look at Nick Montfort's Riddle & Bind. I read this book early in the riddling process and found many of the riddles impossible to solve. Now after writing a bunch of my own riddles, I was pleased to solve many of Montfort's riddles! I was also interested in the different categories of things he riddled about. Riddle & Bind contains many riddles describing parts of the body, while I have not written any bodily riddles; he wrote a series on a book, an eraser, and other objects surrounding the scriptorium. He has a couple riddles about death, and the natural world, which is in keeping with the riddlic tradition.
Most exciting to me is that Riddle & Bind contains a riddle about execution. This is huge because I recently wrote my own execution riddle. Montfort's execution riddle is written in the form of a riddle but it also questions. The execution riddle draws similarities between the execution chamber and the theatre and in doing so, points out the absurdity of certain justifications of capital punishment: "Because we want / for things to not repeat, and think that by / creating such a non-repeating thing, / repeatedly, we'll put an end to lethal / acts on other stages or in other rooms" ("The Spectacle" 8-12)
I am inspired by Montfort's execution riddle and this direction of riddling: asking ethical or existential questions about the modern world, our rituals, and habits. In his introduction, Montfort writes that he thinks the riddle should reveal "new ways of seeing" (xiii). This is where I think the power of the riddle lies!
I totally agree that riddles are powerful because they make people see things in new ways. I however, cannot write them. I am amazed that you are writing 100.
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