I would like to add my 2 cents here.
I believe that what the OP is complaining about is that the guy in his office has had the machine for over a year, and through all of his helping has never bothered to actually absorb the advice given or FUCKING BUY A PEN AND WRITE IT DOWN! (major pet peeve of mine)
::ahem:: sorry 'bout that…
Anyway, age aside (I have seen this phenomenon in all ages) I have an anecdote about how I dealt with a similar situation.
When I was in retail pharmacy work, I had a co-worker who was CLUELESS about computers. That’s OK in my book- I was clueless about 10 years ago, and I remember what it was like. So I’m the pharmacy “computer geek”, and each and every time this woman had a question, she would call me over (away from my work) to ask. She needed help doing absolutely everything- entering patients, insurance, etc.
That was OK the first time. And the second. After about the 100th time of nicely explaining the SAME EXACT ANSWER to her (she needed to be walked through/hand held through absolutely everything) I got an idea. She was dangerously close to losing her job because she wasn’t picking up on the computer stuff- I didn’t want that to happen because I really liked her.
The problem was NOT that she was stupid (I don’t think), she was deep down afraid to do anything without me standing there telling her what to do. I got a bound pack of index cards and wrote down STEP BY STEP exactly how to do the procedures she was required to do. It took forever, but was well worth it.
I gave it to her and said “I’m not always available to help you when you need it- from now on, I want you to refer to this book when you get stuck. This is your own personal “Suzette” (that’s me) and whenever you think to yourself “I wish I could ask Suzette how to do this”, just realize that all you have to do is open up the book, flip to the page you need and there I am- telling you exactly how to do it. Trust me, I thought of everything for you”
She was nervous at first, but soon discovered that I had indeed written down everything I had told her over and over again. After about 3 months of constant use of the book, she no longer needed it and passed it on to another person who needed it. Years later she told me that she never forgot how much I helped her, and thanked me for not losing my patience. It made a big difference in how she viewed computers- she felt smart enough and confident enough to tackle it on her own.
Sometimes you need to work out a solution after you’ve banged your head against a wall long enough 
PS- I don’t mean to sound like some kind of saint here- the guy I work with now is clueless, and never writes down what I tell him. I told him yesterday that if he didn’t buy a fucking pen and a pad of paper, I wasn’t answering another single question again. Ever. There has to be SOME effort on the learn-ees part, you know? It’s a two way street.
Love is like popsicles…you get too much you get too high.
Not enough and you’re gonna die…
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