I was working on a political campaign that required me to move to another state for a few months, but provided no housing for me while I was there. I contacted a (female) friend from middle school and she graciously agreed to let me sleep on an air mattress in the living room of her one bedroom apartment while I was working there.
There was a guy that worked with me that was very nice, but I had no romantic interest in. We would gchat occasionally, as I did with most of my coworkers, and the frequency of our chat conversations increased as the weeks went by. He began to invent excuses to come by our office (he worked in an office in another part of town) and would camp out at my desk while I was trying to work.
A group of coworkers were having dinner at a nice restaurant one night and he offered to give me a ride. I told him "that's ok, where I live is totally out of your way," but he continued to insist on carpooling because "parking is difficult there."
I gave him the address of the apartment and he showed up almost a full hour before he said he would, as I was getting out of the shower. I told him I wasn't dressed and that he should come back later but he kept insisting that he "didn't mind." Keep in mind - I'm currently living in someone else's living room. There was absolutely nowhere for me to do my hair, makeup, etc. other than in front of this guy. It took about 4 times of asking nicely before I finally said "I really need you to leave until I'm dressed." He then waited in his car until I was ready to go. I offered several more times for him to go ahead and I would drive myself, but he insisted.
Of course, arriving at the dinner together, everyone we worked with assumed that we were dating. I tried to sit apart from him but he engineered it so that we were next to each other. When the bills came, everyone else paid separate, but he had already paid for my meal secretly when he had gone to the bathroom. Luckily, I managed to shake him at the end of the night by essentially sprinting out of his car to my apartment.
Fast forward to election night. We had a big watch party planned and we had all booked rooms at the swanky hotel next door because we figured no matter what, we would be drinking and we had earned some luxury. I was so pumped when I checked in because they had a claw foot tub in the bedroom with a huge TV set into the wall above it. We had been working 7 days a week for months and I had been sleeping on a deflated air mattress this whole time, so I felt entitled to treat myself a bit.
The results come in, we lost, we're all drinking at the hotel, I say my good nights and go upstairs. Moments later I hear a knock on my door and it's him. He says his roommate brought a girl home and he's not allowed back in his room, if I don't let him in he'll have nowhere to sleep for the night.
And that's the story of how I spent $400 on a hotel room and spent the night sleeping fully clothed in my jeans in a bed with a wall of pillows between myself and this guy.
I'll give him credit, he never physically tried anything, but dude could NOT take a hint.