What's your silliest conversation with a "customer representative"?

[nolabear]

I just got off the phone with a salon where I get my hair cut. When they answered I got an immediate recording that said a rep would be with me shortly, and the hold music came on. Since it was a well known hair salon I laughed at the fact that the hold music was "The First Cut is the Deepest." When the young woman came on to make my appointment I said as much, that I'd gotten a chuckle out of it and did they do that on purpose or was it just a coincidence? I swear, you'd have thought I was speaking Urdu. It really threw her, and she wasn't even one of those droids who just keep reading the script. She just couldn't be a person-to-person. Got me to thinking about those people who cannot have an actual conversation, make an actual connection with a customer.

My favorite thing when my youngest son was about three and could talk the paint off a wall was to just hand him the phone when I couldn't make an impression, and see how long he could keep them going.

Any good stories of customer rep interactions?