My boss is also brain-hurty about computers. She buys a lot of them for use at the office and knows they're important to have. She's quite paranoid about viruses and downloading things from the Internet in general. But, she doesn't like/trust the anti-virus software we have (mandated by the company). So, she's afraid of viruses... but she doesn't want us to keep the anti-virus software updated... so she just keeps some of the most important computers unplugged from the Internet. So they never get any kind of software updates. But, you know, those could be viruses in disguise, so... And she won't hire or designate anyone knowledgeable and make it their job to maintain the computers responsibly. Or ask the company IT guys to do it for us, because they might want to do extra stuff (mandated by the company!) that she doesn't want.
Another one. There's a built-in projector in a room she uses three times a week. It's been acting weird lately, because it's old, and the blinking or whatever actually makes her nauseous and dizzy. She complains about it to me every single time, all day. She complained to the IT people and made them order a new one (at their expense). Which they probably should have anyway, but she dreads going down and using the old one each day until the new one arrives. I said, "What about that [new, modern] portable projector we have? You could take that to the room and set it up." Oh, that's way too much trouble to go through every time! She'd rather get nauseous and dizzy and complain about it to me three days a week, apparently.
On a different subject, a co-worker really made my brain hurt about food on a conference trip we took together. She has religious restrictions on food ingredients but her way of dealing with it was so inconsistent. First, although we'd discussed the food options and her restrictions several times well in advance, she did nothing to help herself beforehand, like bringing her own food, looking up menus for chain restaurants that would be nearby, or contacting the conference management to ask about the food they'd be providing. Then she would do stuff like refuse to eat the provided breakfast pastries because they might have a forbidden ingredient... but then happily chow down on sandwiches, i.e. bread, without asking about the ingredients. She had a meal at one place she really enjoyed; and only when we went back there a second time did she ask about the ingredients and learn that what she'd eaten had a forbidden thing in it (so she had to get food from somewhere else). Or she'd ask me if I thought something had a forbidden ingredient, instead of asking a server (to which I said, "I don't know. You should ask the server"). Twice she wanted to order a "burger" to eat... she's a vegetarian. The descriptions didn't say anything about meat, she claimed. Yes, she is from another country, but she's lived in the US for at least three years, as an adult (married, small child, PhD).