I had to go to mediation a few weeks back to rid myself of a long-gone ex-business partner who (in the course of dissolving the old company) was suing me for a lot of money in hopes to get me to settle for some sort of payout. In mediation we finally agreed that I would pay him to go away, since it was cheaper than continuing to pay my lawyer and deal with the ultimate cost (and risk) of a trial. I rationalized it by comparing it to paying an exterminator to have rats removed from your attic.

He appeared to have left the mediator’s office once it was all settled, and I made my move for the men’s room. We ended up passing in the hall (awkward) and reflexively I gave the usual guy greeting of “how’s it going.” I realized what I had done a few steps later.

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FML. I just gave someone an unearned payday to make him go away and then I asked him how it was going.

I stayed in the men’s room until I was sure the elevator had left.

So what’s your story of saying stupid things in awkward situations?