I have a difficult time with dentistry. I accept that, for the most part, it's me and not the dentist.
That said, in high school, I went to have a filling done and the dentist missed the nerve 3x when trying to give me novacaine and began to drill before the tooth was numb.

A couple years ago, I was having my first crown put in and the tech was struggling to remove the temp. She had climbed up on my chest and I think she was using pliers when the senior tech came in, tapped her on the shoulder and said the dentist wanted to see her. Moments later the temp popped right off.

My current dentist is aware of my anxiety issues and gave me a couple little blue pills (xanex?) before getting started. Things were a little better. A coworker has also suggested I look into kratom, which can be used to treat anxiety and pain to some degree. In Washington state, it's legal and I bought a bag of capsules for < $20. I tried the white vein and wouldn't describe the experience as a high or debilitating relaxation.

I broke two teeth within 2 days of each other, needed 2 crowns: $2600 later...

Ugh, dentists. In the midst of an extraction—about halfway—local anesthetic stopped working. He injected more, and I accidentally kicked him: still not working. They get out the nitrous, and I’m excited, finally some pain relief.
No. No effect on me WHATSOEVER.
So he finished fast as he could, but PAIN. I had to pay too, least he could have done was give a discount.
Next dentistry was under actual anesthesia. $$$$$.$$