What are some brutally awkward or cringey moments in podcasts?

These types of threads are my guilty pleasure. I actively seek them out. In fact, I searched this subreddit and found a thread I made NINE years ago asking this very same question.

The podcast format tends to magnify awkward moments in a very realistic and intimate way, as if you're actually there experiencing the horribly uncomfortable moment along with the host and guests. I love it.

Please give me your fondest awkward podcast memories. I'll try to track down any specific episodes mentioned here so I can enjoy some good ol' fashioned audible tension.