Not as funny as some other ones, but at least it's original
As a student pilot, I had my share of radio blunders. Here is one.
I'm returning to my home base on the last leg of my first solo cross-country. Due to stronger winds than predicted, later start than anticipated, and lower a/c performance than published, the flight has taken longer than I thought it would. I realize that I might end up cutting it a little too fine with respect to the search and rescue time, so I decide to call up a flight information centre, give them a position report and a new ETA.
Me: London Radio, this is C-XXXX, position report.
London Radio: C-XXXX, go ahead.
Me: London Radio, C-XXXX is on a VFR flight plan, en route to so-and-so airport, at such-and-such altitude, over such-and-such town, yada-yada-yada (where yada-yada-yada is the rest of the relevant details)
London Radio: Roger.
So far so good, and I should have just stopped there, of course, but because this is the first time I strayed any distance from my controlled homebase, that exchange just didn't feel right. Before this flight, talking to someone on the ground equalled talking to the ATC, and the voice on the other end always gave me instructions at the end! Plus, that last "Roger" didn't sound like an end to a conversation; the intonation seemed to be implying that there was more for me to say... and I already said everything I thought I was supposed to. So, knowing full well that I'm doing something kinda dumb, I keyed the mike and meekly asked:
Me: Um, London radio... is there anything you would like me to do?
If I were London radio people, I probably would have said something along the lines of "draw me a bath". But they seemed perplexed, not amused, by my silly question, and just mumbled something along the lines of "Um, no, C-XXXX, it's all good, have a good flight".