In my formative years in the IT field, I worked at the help desk for a university, my alma mater in fact. Help desk sucked, but hey, everybody has to start somewhere.
One of the services the IT dept. from the university offered was cheap dialup internet access (late 90s here) to students, employees, and retirees. One day I get a call from a retiree who had just gotten a new computer from her son and had signed up for the internet service. One of the techs didn't want to deal with her, and pawned her off on me. We gave out cds and instructions on how to set it up, but some people just couldn't pull that off. I start trying to walk her through the setup, and nothing is working. I was going crazy trying to explain simple stuff, and she just didn't seem to get it. I had her check the CD, and it was ok and said "Windows setup cd". The light bulb went off after I had to explain the concept of "right click", and she told me her mouse only had one button. I asked her to describe her computer, and it was a pretty, shiny blue, and everything was all in one piece.
I finally got her to come back and get the Mac setup cd, but it didn't end there. Then came calls to setup email, how to do a word processing document, and more. And she would only talk to me. I felt like I had an elderly stalker. It all paid off, though when she actually showed up at our office one day. She wanted to personally thank me by giving me a huge bowl of home made chocolate chip cookies. I had fun reminding my coworkers that since they didn't want to deal with her, they didn't get to sample any of the cookies. And they were so delicious.