I had one touring partner who I was unhappy with, but he was never boring. The idea was to cycle to Key West and back, about 500 miles total. First, he had needed maintenence to do on his bike, which he had plenty of time to do, which he did not do. Whatever I advised him to bring he left behind. That which I told him to leave behind he took. Then, when we got caught out in some nasty weather he bummed part of my gear leaving me at a disadvantage over the weather because I had brought the minimum. He packed more weight of gear on his bike than I would carry on an around-the-world expedition. All this against my simple advice for maximizing the enjoyment of the trip. All along the way he ignored the voice of experience. I tried my best to listen to the guy and go along with his suggestions, but he get getting us off track. We stopped at Dunkin Donuts. I had an iced coffee. He had a hankering for some kind of sandwich which just had to come from one certain fast food chain restaurant, so he asked the young woman behind the counter where he might find said restaurant. Of course, she gave him detailed directions, and it was only four blocks away? Outside I tried telling him the directions were off or possibly even bogus. We had quite a heated discussion, but I ended up taking a 90 degree, four block, four very long blocks, turn off our path, and no such restaurant. You could stand in the middle of the road, and for as far as you could see, no such restaurant. . He became so crazy he claimed it was there anyway, seriously. He kept lagging far behind, the weight, yet he did not carry a patch kit and pump. He kept jumping curbs, again against my advice, and broke his rear rack requiring time to stop and buy another one.
We were south of Miami at night when we came to some sort of wildlife conservation area. It was fenced, but knowing it would probably be gated with one of those easy to get through / over, metal bar Z gates, I took us around the perimeter looking for it. It was dark. We were looking for a safe place to sleep for the night. But no, he insisted on camping near a path in the woods. Out of kindness I agreed. We hefted out bikes and gear over a low white fence. The next thing we knew some deranged sounding homeless man came charging out of the bushes, threatening us with serious bodily harm and even death. We reasoned with him and calmed him down. At the end of a 10-15 minute talk I asked him where the gate was. He said. We went there and had a good night's sleep.
We got into the Keys. He was complaining about the road and the traffic. Well, yes me too. We got to a convenience store where he saw egg salad sandwiches for sale. The cashier told him they cost two dollars less at the deli in Publix three miles back down the road. He wanted to back track, and did, to save two dollars because he packed too much into his panniers with no room for food.
One day, while camp was set and I was about a mile and a half away reading a book at Barnes and Noble, he got into some kind of a row with a group of teenagers with paintball guns. This was at the campsite. He chased them through a bushy area, with a shovel. One of the kids dropped a cell phone. He picked it up, and dialed 911 in a hale of paint balls. The police showed up. Jack wanted to press charges againt the teens. The officer said he would press charges against Jack for use of a weapon, the shovel. Okay, so I got back later and found out what had happened. Later, some guy from the sheriff's department walked into our camp. He said---Jack! You have two hours to clear your camp and leave. I will be back here in two hours. If you are still here, I will arrest you. The officer did not say anything to me. We left.
I split from this fellow the night before we got into Key West. The next morning I went into KW, toured the island, then turned north for the 250 mile trip back in 2 1/4 days. He took the old grey dog, along with a three foot in diameter roll of rubber-foam mattress he found in the woods, wrapped in a plastic garbage bag. He arrived by bus in Fort Pierce, 18 miles from town because the bus doesn't stop here anymore. He called his buddy Mark to come and get him. Mark told him to ride his bike. So, he did.
There were quite a few other matters. I think you can get the idea. No one single act of ignorance or neglect amounted to much, but the many taken together and what that seemed to suggest could not be ignored. It was a steady line of things which told me it would probably be the same in KW, and likewise on the trip back. I had cycled over 32,000 miles by that time. I cannot remember having had any such problems on any tour after having learned what was what for cycling and free camping. I had an excellent grasp of what to do and what to avoid; however, it was all for nought because of the other guy's willful ignorance.
It was kind of disgusting, but it was not boring.
