The 5 Naughtiest Medieval Riddles, Ranked
The Anglo-Saxons were beautiful poets, proud warriors, and incurable horn-dogs.
At some point between 1072, when the Bishop Leofric bequeathed “a large English book about a bunch of stuff, written in verse”1 to the Exeter Cathedral Library, and the 19th century, when we all started to think that Anglo-Saxon-core was actually very retro chic, somebody decided that the single most vitally important source of Anglo Saxon literature made an ideal coaster for their beer. It is sadly lost to history whether this was the same person who used The Exeter Book (vigorously, judging by the knife marks) as a cheese board, but if it was I’d like to pause for just a moment to give it up for an absolute legend who was slicing Wensleydale and sloshing brown ale all over the world’s only existing copies of The Wanderer and The Seafarer while he scanned through the riddles for the naughty bits.
The naughty bits, of course, are why we’re here today, so I’d like to invite everyone to hack away at a nice piece of English Stilton and messily quaff a stein of Bitter over whatever priceless manuscript you happen to have handy and join me for a ranking of the five smuttiest “obscene riddles” in a book that was (I’ll just point out again because it’s funny in this context) famously donated by a Bishop to his Cathedral Library.
(N.B., these translations are my own, and I’ve made a number of choices both to sound modern and to capture some of the fun alliteration and assonance of the originals, so please be gentle with them if you’re an actual Anglo-Saxon scholar!)
5. Riddle #45 (the one with the boneless bump)
So I’ve heard about this thing that grows in the dark
Swelling and standing to attention, pushing up its covering.
On this boneless bump a girl did grab
Hungry with her hands, a courtly daughter
Covered it in cloth, a mushrooming mound
As fun as it is, this riddle comes fifth in our ranking because it’s basically just the Anglo Saxon equivalent of a winky-winky Great British Bake-Off cold open. The answer, of course, is DOUGH, and all that covering in cloth and standing to attention in the dark is a roundabout way of saying what Paul Hollywood told the Great British Food Awards about proving drawers in 2021:
"We only use proving drawers on the 'Bake Off' so that contestants can get everything done in time. Put your mix somewhere cool with a bag over the top and wait for it to double in size slowly — again, that's where the flavour comes from!"
Sexy!
Old English Literature scholar Megan Cavell has pointed out that the high status of the courtly daughter (þeodnes dohtor) in this riddle may have extra significance when you consider the Anglo Saxon origins of our words “Lord” (hlaford) and “Lady” (hlæfdige) — which mean, literally, “Loaf-keeper” and “Loaf-kneader.”
4. Riddle #44 (the one with the thigh oddity)
An oddity hangs by the thigh of a man,
Under the lap of its lord. Up top, there’s a slit;
It’s stiff and hard; and hardness serves it well
When homeboy hitches up his robe
Past his knees, he wants to greet
The old hole with the head of his dangler,
Which fits perfectly, as it always does
If I had a nickel for every time I stumbled home drunk and fumbled to get my dangler into the keyhole, I’d have more nickels than I’m strictly comfortable talking about, but, yes, the answer to this one is KEY. “Babe?” you are often heard saying to your significant other as you haul the groceries out of the trunk, “Could you hitch up your robe and grab the oddity that hangs by the thigh of a man? I have my hands full.”
3. Riddle #61 (the one with the manly master)
I used to be locked up by a lovely lady
She laid me snug in a chest till she dug me out
With her hands to give me to her guy
Her manly master, just as he asked her
Then he’d thrust his head up in my guts
Pushing it under and tightly inside me
Providing he could keep it up, you’d find me
(Looking snazzy) filled with something
Kinda fuzzy. Whatcha think I am?
The “snug in a chest” bit feels like kind of a stretch for the double entendre, but the word on the street (by which I mean “the opinion2 of respected Anglo Saxon scholar Edith Whitehurst Williams”) is that while it “cannot be applied in a literal way to the secondary meaning … it is undoubtedly a metaphoric statement for the lady’s great modesty which is set aside only in the proper circumstance — when her lord commands.” Anyway, the answer is SHIRT. You know — that thing your wife pulls out of a chest and demurely hands you in the morning so you can stick your head into it, fill it up with your fuzzy, hairy torso, and presumably get on your way to the office.
2. Riddle #25 (the one with the rubbing)
I’m an exciting sight, delighting the wifies
Nice for the neighbors, noxious to none
In the town save the one who slays me
My shaft is steep, and I stand up straight in the bed
With hair down there — She dares,
(The very pretty peasant’s daughter,
A gutsy gal) to pull me up,
Rub me to redness, tickle my tip
And dip me in darkness. Soon she’ll
Feel my presence, the frizzy missy
Who keeps me; moist now and weeping
If you’ll accept that people used to get a lot more excited about the appearance of an ONION (this was before Netflix, remember), the rest of this riddle falls into place. They’re hairy on the bottom, they stand up straight in the garden bed, and they’ll make you weep. Do they absolutely need to be energetically fondled by gorgeous, headstrong peasants’ daughters in order to be the most effective onions that they can be? I would argue no, but this riddle really goes the extra mile to get its PG-13 rating, and that makes it the most pornographic poem about a gazpacho ingredient in well over a thousand years.
1. Riddle #54 (the one with the diligent dude)
A young man strode right up to the corner
Where he knew she stood; strutted up
This strapping dude, and with both his hands
Set aside his slacks, and thrust something stiff —
She’s just standing there — under her girdle
He worked his will as they both wriggled
Dude was diligent, coming through in the clutch
Serving her well, though he tired at times
With every stroke; strong to start
But weary from work. Growing now
Beneath the girdle was something good guys
Gladly get, and cherish in their hearts.
The smuttiest riddle in the Exeter Book is actually describing a particularly strenuous session with a BUTTER CHURN, which means that our hero is just a diligent dude doing his damn duty by wrestling enthusiastically in the corner with a Medieval food processor so the fam doesn’t have to eat dry toast. Absolutely nothing to see here, officer. The guy was just sweatily manhandling a large kitchen implement. Not entirely clear why he took off his pants to do it.
“Mycel Englisc boc be gehwilcum þingum on leoðwisum geworht”
Hilarious. Who says medieval literature is boring. Thank you for the time to ferret these out and congratulations for being the first substack specifically to apologize for possibly offending Anglo-Saxon scholars‘ sensibilities.