A lot of episodes, especially the ones where the people being featured sound fairly young, give me really intense second-hand embarrassment, but it's never been so bad that I've had to stop listening. I was a stupid, self-absorbed teenager who also happened to be something of a musical child prodigy (no, seriously - Ask Me About My First Professional Tour Which Happened When I Was 11*), so the Sub-Sub-Pop episode just made me cringe really hard.
But the only one I've had to outright stop listening to was the most recent one. I'm severely phobic of bugs, so I mean, I don't really know what I expected. I thought it would be uncomfortable in a funny sort of way, but it was just kind of terrifying to me.
*Like most former child prodigies, I dropped the thing I was prodigious at as soon as I became old enough to make my own decisions, and now live a pretty mundane life, which is awesome.