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Take my glasses off on the bridle way and then find them again, a new low has been hit.
It gets even lower if you forget to put them back on, and don't realise for half an hour (wasn't me, honest).
Fight with my tubeless valve for about twenty minutes. Leave a sealant covered homemade tyre insert on the side of the trail (a short loop in Sheffield) for a little over an hour. Then apologise to the other riders I saw, explaining that it was my insert and I would be discarding later. Then ride to the nearest bin (further than I expected!) with the insert covering most of my right leg in lovely sealant. Mmmm. Delightful! Still love tubeless, I just now put a few psi more in the rear tyre rather than attempt to use a different insert.
For real puncture hell, try doing it with the rear wheel of a 1940s full chaincase 3 speed bike in the rain and dark when your only light is the one bolted to the front of the bike which only works when the front wheel is turning (Dynohub).
Anything since has been a breeze.
My puncture hell was fixing a tyre on a tourer next to a busy main road in Devon and have it start hailing. Luckily I was suitably dressed for the weather because it was..... July.
Use every pair of dry socks on a bikepacking trip trying to dry the tube enough to get a patch to stick.
Fix about 20 after riding through gorse bushes.
#pretubelessera
Pulling 40+ goat head thorns out of EACH tyre (two bikes) after girlfriend took a shortcut trail when we were riding in Utah...
At least we did it in the comfort of our motel room with a couple of adult beverages each after getting a lift in the back of passing stranger's pick up truck...
I got a slow puncture that started hitting the rim on my way home from the pub once. Had my mini pump, so decided to puff it up a bit, except the head bits were set for the wrong valve. In my pissed up state I managed to drop them in the grass while adjusting them. Having already flattened the tyre fully trying to blow it up before realising about the valve problem, I walked home.
In the Pyrenees, halfway up the climb of Cirque de Troumouse (beautiful)... a puncture. Getting the tyre off, I slipped with the tyre lever and my thumb hit one of the spokes very hard.... a long, deep cut in my thumb, pouring wih blood.
Fortunately I had a rubber glove with me and this allowed me to change the tube and get going again but blood dripping despite the glove... turned round and rode back down. The next day the weather changed and the storms came in... I never did get to the top of Troumouse. Gutted.
... flag down a passing septuagenarian to borrow his tyre levers after mine had gone brittle in the cold and snapped. I was on a long winter training run and still about thirty miles from home, close to tears as my hands wouldn't even work to change gear.
Luckily this wool-clad auld bugger stopped and lent me his metal levers. He insisted I kept them as he couldn't wait for me to faff around because the cold was playing hell with his rheumatism; luckily I managed to get the tyre off before he got away, salvaging a mere shred of dignity.
Boxing day up early for a ride, frosty morning. Puncture. Tyre lever snapped and the broken bit hit me in the eye.
For what ever reason my glasses hadn't steamed up and I still had them on.
That was a win.
Scratched the lenses deep enough to ruin the glasses