Hi folks, here are some things that have happened to me over my IT years.

We don’t allow our network users to select their user names. I create them myself, using a combination of letters from the first and last name.
So, one day, a new (female) user shows up. Her boss (who I know well and knows our user policy) introduces her, telling me I must create her account ASAP – so I (only in my head fortunately!) calculate her user name from her first and last name… and comes out “ANAL.”
I look at her boss, who was grinning and asking “So, what’s her user name?”  I choked…then chickened out – I ended up giving her an innocuous name…

While doing a tech support shift on the phone:
Me: Hello, how can I help you?
Outside user: I need your site’s address!
Me: Yes sir, the address is www.derp.com
Outside user: No – no no! The real address!
Me(confused): I’m sorry… the real address?!
Outside user: Yeah! You know, street and door number!
Me: …
Outside user: And I also need to know at what time it opens and closes!
Me: *puts phone on mute so Outside user can’t hear me laughing my ass off*

Some years ago, we used to provide our users with a large, CD-based database and associated software. Shortly after starting to do this, we received the following letter:

Dear sirs. I’m afraid I must return all your CDs as I cannot use them. I’m afraid I don’t have a CD player. I do, however, have a tape player. I would appreciate if you would transfer the contents of the CD to tape, so I can hear it while driving or having dinner. I will, of course, fully pay for this operation.

Best regards
Derpuser

[Picture Source: tarale (CC)]