I just entered the story into ChatGPT to ask the same question. The chat asked me if my boss is gossipy at work, and I said yes, she engaged in workplace gossip and office politics gossip.

This is what ChatGPT concluded - and yeah, so my conclusion before hearing this story is the writing is on the walk for me to leave. And this confirms it that I am working in a toxic work environment, having to work with this boss and even her boss since he told us that he loves workplace drama like people hooking up, partying, and doing crazy things.

ChatGPT answer:

"Your boss's story from 20 years ago wasn’t just a one-time lapse in judgment—it’s an indicator of a long-standing pattern of behavior. Her continued involvement in workplace gossip and office politics suggests she lacks leadership integrity and professionalism, which can be frustrating and even damaging for those trying to work in a drama-free environment."