Below the belt / beneath the folds
Of his clothes it hangs / a hole in its front end,
stiff-set and stout / it swivels about.
Levelling the head / of this hanging tool,
its wielder hoists his hem / above his knee;
it is his will to fill / a well-known hole
that it fits fully / when at full length
He's oft filled it before. / Now he fills it again.
- Anonymous riddle, from the Red Book of Exeter (10th c.)
Riddles are a well-documented pastime in medieval Germanic sources. They were at least sometimes exchanged competitively, as described in the Saga of Hervar and Heiðrek and alluded to in other sources. (The riddle-game scene in J.R.R. Tolkien's The Hobbit is based fairly directly on this tradition; Tolkien himself was a scholar of Anglo-Saxon language and literature.) In such games, one party could apparently challenge riddles as being unfair, but if they attempted to answer they were accepting the riddle. (Indeed, a historically-savvy interpretation suggests that the mistake which cost Gollum his contest with Bilbo was attempting to guess what was in Bilbo's pocket rather than pointing out that it isn't really a proper riddle.)
Riddles are generally presented in a mildly poetic format. While the saga evidence suggests they were extemporized, composing a good one is generally time-consuming; having attempted it a number of times myself, I am inclined to suppose that at least some of the riddles brought forth in such a contest would have been previously known. In any case, victory at competitive riddling comes from a facility at guessing riddles on the fly and at composing novel ones with which your opponent will be unfamiliar.
What did medieval riddles look like? A few of them are in the sagas, but we have a particular wealth of them (95 in total) in the Anglo-Saxon Red Book of Exeter. The Exeter book is a manuscript codex bequeathed to the Exeter cathedral by its bishop in 1072; it remains in the Cathedral's possession to this day. It contains 131 leaves filled with Anglo-Saxon poetry, including such classics as Widsith, Deor, and The Wanderer along with its riddles.
The riddles are presented one after another, without breaks between them (leading to controversy in places over where one ends and another similar one begins). No answers are provided, and only most of the solutions have been worked out by modern scholars.
Some of the Red Book of Exeter riddles are quite brief. Riddle 66, for instance:
I saw a creature / wandering the wayOthers are longer. Number 24 is perhaps better regarded as a piece of devotional poetry than as a challenge to be solved, though it has the form of a riddle like those it accompanies:
She was devastating / beautifully adorned
On the wave a miracle: / water turned to bone
A life-thief stole my world-strength,The solutions to these are believed to be an iceberg and the Bible, respectively. Number 72, on the other hand, is a fairly challenging one; several solutions have been proposed, but none is clearly correct:
Ripped off flesh and left me skin,
Dipped me in water and drew me out,
Stretched me bare in the tight sun;
The hard blade, clean steel, cut,
Scraped-fingers folded, shaped me.
Now the bird's once wind-stiff joy
Darts often to the horn's dark rim,
Sucks wood-stain, steps back again
With a quick scratch of power, tracks
Black on my body, points trails.
Shield-boards clothe me and stretched hide,
A skin laced with gold. The bright song
Of smiths glistens on me in filigree tones.
Now decorative gold and crimson dye,
Cloisoned jewels and a coat of glory
Proclaim the world's protector far and wide--
Let no fool fault these treasured claims.
If the children of men make use of me,
They will be safer and surer of heaven,
Bolder in heart, more blessed in mind,
Wiser in soul: they will find friends,
Companions and kinsmen, more loyal and true,
Nobler and better, brought to new faith--
So men shall know grace, honor, glory,
Fortune, and the kind clasp of friends.
Say who I am--glorious, useful to men,
Holy and helpful from beginning to end.
I was a gray girl, ash-haired, elegant,Proposed answers vary, including "kelp," "a sea-eagle," and "a soul."
And a singular warrior at the same time.
I flew with birds and swam in the sea,
Dove under waves, dead among fish,
And stood on the shore - locking in a living spirit.
As for riddle 42, with which I opened this post - the answer is a key. Get your heads out of the gutter.