Part 1.
I'll share one rather long story to hopefully get this thread going. I'll change a name or two to protect the guilty here. lol Bob and I met in college nearly 27 years ago. I was in my early 20's. He was in his mid to late 20's. He was an Episcopal deacon. He did have the title of "Father". He wore a white color on the job and all. He came from a very wealthy family but of course was not wealthy himself. Because of his silver spoon upbringing as a child and teenager, he still had what we would call today, "Champagne tastes on a six-pack budget". lol We struck up a friendship. The friendship evolved to where we were pretty close. It did reach a point where we became kind of friends with benefits. We were not boyfriends. Just a good friendship.
I visited him often when he lived in his apartment alone. He was always better off financially than me in college. If things got tight he just called his parents. When he later got one roommate in particular (who was also a young college student) he complained to me about the thoughtlessness of his roommate and the roommate's girlfriend. Talking about annoying habits like the roommate leaving his partial dental plate just sitting on the kitchen counter outside of the case. He said the roommate's girlfriend would eat his food without asking. He said that he resorted to hiding his jars of peanut butter under his bed in his room just to keep it away from the other two. lol He said the girlfriend would pour a tall glass of milk that he bought and paid for, drink a fourth of it and then just walk away and leave it.
I felt so badly for him that he had to put with people like that. My roommate experiences up to that point in the dorms and in apartments had overall been very positive. Toward the end of our college days we did not have "benefits" anymore. Things had evolved into just a platonic friendship. Fast forward about 2 years after my graduation. Bob and I had lost touch for quite a while. I was working a full-time job on salary that was kicking my ass with 55-65 hour weeks and relatively low pay. He called me up out of the blue at work and asked to meet up. We did.
My situation was that I was in a 2 bedroom 2 bath apartment by myself. The roommate I moved in with graduated and got a job in D.C. I had lined up another roommate before he left and then at the last minute he backed out. I was royally screwed. It took over half my take-home pay just to make the rent. Let alone utilities, gas for the car, insurance, food etc. And as I say I wasn't making very much. I hadn't found another roommate yet but was actively looking.
Bob was in a bad way too. He was renting a bedroom in a house with two young female roommates. The women were very nosey and always going in to his room to snoop when he wasn't there. He said he would keep the door closed when he left. On two occasions when he came home he would go into his room, open the closet, and the roommate's cat would come scampering out. He said the one roommate's boyfriend was picking up on the fact that he was gay and was hitting on him for "a piece of the action" as Bob put it. He really wanted out of the house, even if it meant breaking the lease he had with the women. Again I felt sorry for his terrible luck with roommates. The stars were aligned in such a way that it made perfect sense for me to offer him my place.
Even though I didn't like the idea of helping someone break a lease...I did help him smuggle his stuff out. He didn't have the nerve to tell them he was leaving. I got him moved over to my place. Little did I know that he of all people would be a roommate from hell. I would almost immediately start to regret it. I found out that he had no stable job or income. His life was in freefall mode even though I didn't know that at the time. He wasn't making anything of himself. I even had to buy groceries for him when he moved in. Needless to say, I was getting no rent money.
I later found that he was on the outs with his family because they had sent him about $14k dollars cash to buy a car a year before, and he used it to take a boyfriend on a first-class trip all over Europe. So they had cut him off. Of course once the boyfriend had gotten the all-expense paid trip to Europe out of Bob, he was long gone too. Ain't love grand? haha
Then I got my first phone bill. Normally it was about $30. It was $240. I freaked. I immediately said, "You can pay for this. Right?" He said yes. He had bene calling family in Canada at international long distance rates during the peak business rate hours and had called long distance within Florida and all over the country. Stupidly I actually gave him the phone bill and told him to take care of it. He said he took care of it. Then he met some guy at a club and was staying over at his place several days and nights a week.