This is becoming commonplace, particularly in coffee shops. I make a very grumpy point of asking "May I please have a doobriewhatsit?" in polite earshot of the muppet who said "Can I get a Frappalappadingdong?"
I find this really annoying, too? The raised inflection? At, like, the end of every, like, sentence? What? I'm, like, what, like, massively irritating?
Exactly! If one could care less about something, it therefore indicates that one actually has a definable level of care about that something. If one could not care less about something, it illustrates the point that one couldn't give two hoots about it. I see it quite a lot in thriller/crime novels and I get terribly annoyed with myself for getting annoyed by...oh, you get the picture...