When I drove Oregon for work a couple years ago, I was caught off guard by this.
I had crossed into Oregon from California and drove until I needed to stop for gas. I pull into this quik-mart/ gas station type place and hopped out to start pumping. I had removed the cap and before I could reach the pump, this grubby older guy asked me what I needed. I was confused and thought he was gonna ask me for spare change.
I told him I was just getting gas, and he grabbed the pump. I was now thinking that he was one of a different version of one of those bums who will wash your window when you don't want them to, then expect money.
I told him that's okay, I'll get it.... and he looked at me like I was from mars. He then explained the law to me. He said it's a heavy fine if you are caught pumping your own gas. I cant remember the fine..... $5000.00 or something?
I asked him why it is that Oregon has this law, and he said something along the lines of "trust me, you don't want most people trying to pump their own gas. I saw one person pump gas all over the roof of their car once". Yeah, sure you did I thought.
When he was done, I was wondering if I was supposed to tip him, or what. It was awkward, but after a couple of days I got used to it yet hated it.
Some of the places I went to had only one pump jockey trying to handle about 5-10 cars. More than a few times I sat in front of a pump either waiting for some moron to pump the gas, or I was sitting with the pump sticking out of the car, having completed pumping, and waiting for the guy to come take payment. For me, it was just a pain in the arse.
I guess if you live there it just becomes normal, but for me it was irritating and seemed like really sensless.