Four flats in one day
The first one was actually pretty hilarious. We were at 90th and Mackinaw on our way to Wolf Lake when he called for a halt upon finding that the pressure in his rear tire was suddenly and inexplicably low. Here of all places, I thought, eyeing the flashing blue light of the police camera down the block, this is where you got your first flat tire. He dragged his bike onto the sidewalk and flipped it over. Sticking out of the sidewall of the rear tire was a toothpick. A toothpick! I made fun of his skinny, high-pressure roadie tires. (He was running 700x28. It's a long story.) Between the two of us and our three working thumbs and four tire levers we managed to pry the tire off. He even had a spare tube, leftover from my brief stint at trying to be a roadie. Getting the tire back on was marginally easier. He reflated the tire as best he could with my hand pump. It was squishy but seemed ridable for the day, provided we stayed on pavement.
The second flat was kind of my fault. The flat pavement ended. Myself, my cyclocross bike that I don't use for cyclocross, and my ridiculous huge double-walled treaded reflective-striped 700x35 unholy tires of the damned were undeterred. I wanted to keep going, of course, and see how far across the lake I could get. He was sensibly hesitant. "Well," I said, as remounted and pushed off, "you stay here; I just want to see how far this goes." He wasn't going to do that, of course. We found out that the causeway went practically to Indiana, then turned around to head back. That's when I noticed that his rear tire was flat again, probably a pinch flat from riding underinflated over rough ground on a completely unnecessary detour across the lake.
On some level, I honestly thought he'd be OK. The recommended pressure range of the tires that came with his bike is pretty wide, and all summer he's demonstrated countless times that there's no pile of rubble, no thicket of weeds, through which he can't follow me, even though my bike is supposed to have all the special awesome off-road capabilities. But there's no rationalizing or arguing with the laws of physics. PV=nRT, and that's that.
So we walked back to the pavement and found a bit of shade under a scraggly young cottonwood, and got to work with the patch kit. It took a couple of tries; he was a n00b until recently, and I always prefer to carry several spare tubes. Consequently, neither of us have had much practice patching tubes. There must be a knack to it that neither of us have figured out yet, because it deflated again as soon as he flipped his bike over. So we tried patching the other tube, but alas, it also refused to hold air. We also began to notice that the repeated bouts of frustrated hacking with the tire levers had begun to strip the rubber from the tire bead. I phoned a friend of a friend, who advised that the tire was probably close to finished, although he might be able to ride home on it. But when the second patched tube failed, we gave up and started walking.
Was it bad luck, or just bad karma? He expressed interest in the Panaracers that I tried and failed, because he was there when I bought them and heard when the were alleged to be nearly bulletproof (certainly tiny rock-proof and toothpick-proof), especially if he's going to need a new tire anyway. However, I am wary, given that I've already experienced bad luck with one of them---it was so difficult to wrangle on the rim that I couldn't even do it right, which caused the tube to explode and me to shy away from my new bike for weeks until I gave up and bought new tires. Does he even need a new tire? I find it difficult to believe that a $3 piece of plastic that could barely even pry the bead off the rim could actually damage the bead.
Later, his car died. So it's all moot anyway.