Stupidist was when I was 18 and bought a bike thinking the cute chick who worked in the bike shop downstairs from my apartment would date me if I rode.
In 1976 I lived in Atlanta, I had saved up about $600 bucks between a tax return and working the summer knocking on doors for Jimmy Carter's Presidential Campaign to buy a car. I saw this really hot girl working in the bike shop, I was smitten. So I spent the $600 car money for a used silver 1974 Condor with Nuovo Record and sewups , Bell wool shorts ,jersey and Campy hat. I didn't have a clue what I was doing. But I started riding and pretty soon I was up to doing 25-30 mile rides and hanging out at the bike shop with every excuse I could come up with. The cheapest item in the shop was the jar of leather toe straps on the counter selling for $1 each. I probably owned 50 toe straps.
I had been riding about 6 weeks and one day at the shop she was talking about an upcoming club ride she was going to be on. I looked at the local bike club's news letter and saw they had a ride that coming Sunday starting about 20 miles away. So Sunday morning I got up early and rode the 20+ miles to the ride start. I sign up but I don't see her around anywhere and then was told that a small group of cyclists had just started. I get on my bike and I sped towards the earlier group. I catch up to them a few miles down the road and recognize her Guerciotti. I ride up beside her to say hi and she is astonished. She says " I didn't expect to see you on a century ride!" I said something about it sounding like a nice ride and then I asked "How long is a Century?" The whole group nearly crashed with laughter. Finally someone told me it was a 100 miles. I tried to play cool like it wasn't a big deal and vowed to finish the ride( I was dying inside).
I managed to hang with them untill the first rest stop at 25 miles. At that point I had already ridden more that day than I ever had and I still had 75 miles to go. I dropped back and rode with a slower group to the 50 mile mark, I was really hurting by then. I slowed down a lot after that and by 75 miles I had long been dropped off the back and the rest stop people had packed up and left. I was out of water and feeling really bad, It being Sunday afternoon in rural Ga everything was closed. A couple more miles down the road I came upon a Moose-Lodge that was open. I stumbled in(I could barely walk) to ask for water and after I got the usual redneck treatment they begrudgingly filled up my two bottles for $2. The only food they had was peanuts and fried pork rinds so for another $2 I stuffed my jersey pockets with that and left. Peanuts and Pork Rinds must be a energy food because not long after eating I started feeling pretty good again and picked up the pace a bit and got back to the start/finish almost 9 hours after I started. My plan was to bum a ride back to Midtown Atlanta but everyone was long gone. So the only way home was to ride the 20 miles. I think it took me 3 hours to ride the 20 miles. 140 miles total. I finally got into bed about 10 pm and stayed there for two days.
As for the girl I found out not long after that she was gay. We became good friends and riding buddies for a number of years.