Suckerfish on the Side of Your Whale

Me: "I'm noticing that on your brother's account, your last name is spelled with an 'o', whereas I thought I heard you say yours was spelled with an 'e'. Did I mishear you?"
Caller: "No, my mom spelled my name wrong on my birth certificate."

With such an auspicious beginning, I should have known what to expect. It'd be cruel to post too much, so here's one of the "best" excerpts:

Me: "What version of Windows are you using?"
Caller: "Windows 95XP."
Me: "Windows 95 and Windows XP are actually two different versions. Do you know which of those two you have?"
Caller: "Uh, no, I'm not sure."
Me: "What color is the start menu?"
Caller: "The what?"
Me: "The start button."
Caller: "The what?"
Me: "The button in the bottom left that says start."
Caller: "In the bottom... the bottom right?"
Me: "No, sir, the bottom left."
Caller: "I see the time--"
Me: "No, sir, the bottom left."
Caller: "Oh. What am I looking for, again?"
Me: "The start button."
Caller: "The what?"
Me: "Start. S-T-A-R-T."
Caller: "Oh. I found it."
Me: "Perfect. What color is it?"
Caller: "Should I click on it?"
Me: "No, sir. Please, just tell me what color it is."

At least things got slightly better after that.