The only one I can think of that was really REALLY awkward was the first year I worked at the Collection Agency. I was in my office discussing a debt with a lady, her first time being in front of anyone in the profession of recovery.
We talked for a bit, trying to find ways for her to pay off her student loan or whatever it was, and finally she said,
'well there is just no way I am going to be able to pay it off, so you will have to let me do some trading'.
I was naive, thought maybe she had a vehicle, maybe a quad or boat....
and off came the clothes.
She was down to bra and panties in a few seconds, I just barely had time to start screaming for my Boss to 'get in here right now'.
There was absolutely NFWIH I was going to be alone with her in my office.
Of course he walked in, saw her stripping down, and got the biggest dumbest grin on his face, I was sitting there speechless and this woman is reaching for underwear.
I got her stopped just before any nudity, explained what had happened, and told her that we do not do that here, said she should maybe get dressed and come back another day with money.
Yep. Awkward. And yes she was hot.
In hindsight, 'Dear Penthouse, I can't believe this happened to me' lol