It really wasn't that terrible, but still rather uncomfortable.
At the time I was working for a law firm in the area and all of my coworkers and I went out for drinks. I left earlier than most and took an Uber ride home by myself. A man in his fifties or sixties picked me up and started off the drive by being perfectly pleasant, just making small talk. I mentioned I was just at a work event, so he asks me where I work and I tell him. Turns out, he used to work at that same law firm and he IMMEDIATELY starts bashing them, saying that they're awful greedy people (kinda true tbh) and that he only worked there for so long because of a girl named Jessica.
Now, Jessica still worked there at the time, and she was out with us that night. She could've easily gotten into his Uber by chance.
He goes on to tell me he had feelings for her and starts making really, really creepy sexual comments about her body and his "missed opportunity." Creepy, because this dude is old and Jessica was about 30 or maybe 35. So I ignore it and make sure not to mention that she still works there.
The best (worst?) part is that he then proceeds to tell me that he's still a lawyer, but needed to become an Uber driver because he has kidney issues to pay for. He tells me he's on dialysis a few times a week and will eventually need to be on the transplant list, so he's working multiple jobs to cover all his medical expenses. Totally cool, do you dude. But then he ASKED me - a twenty-two year old woman he just met - for money to help cover his expenses. I was extremely uncomfortable and made a joke like "well, i can give you the fifteen bucks I owe you after this ride is over" but he kept pushing it, saying he knows what kind of money X law firm pays its employees. Then he mentions that other Uber riders have chipped in, and that these "donations" have allowed him to live longer because he couldn't afford treatment otherwise.
Ugh it was so awkward. I half-expected to be robbed or murdered...he was being SO pushy even though I clearly said no... so I had him drop me off in front of "my brother's" house and luckily it ended there.