I recently found this subreddit and I have STORIES.
TL:DR. My boss tried influencing my birthday party guest list with someone I didn't want there. Then make a big fuss about me not being able to invite them, nor hang out with them outside of work.
I left this job last year but I was there for two years. Fresh graduate ready to take on the world.
The first red flags were when my boss (who was the CEO) tried hooking me up with her friend's niece. I organized a birthday party and invited my work colleagues, the CEO, let's call her Dawn. Couldn't come but kept on joking about me inviting her friend who is working with us (lets called her Jean) niece. I didn't want to because: I'm gay. But I played along with no romantic discussion on my part. Jean and I regardless shared good times at work.
Turns out she fell out with Jean's niece at church because the niece thought Dawn was abusing her aunty financially (can absolutely see her doing that, she's extremely greedy). Dawn comes to my office (during work hours) with the CTO and CFO tagging behind and screams that I cannot invite the niece to my birthday party quote “This is Dawn's Empire”.
I agreed because I wasn't going to invite her anyway, but what kind of boss can tell you who to hang out with. Jean was so timid and explained profusely in private that her niece has every excuse under the sun not to come and now Jean can't come either.
This was the first red flag.