One night I had a couple guys sitting on one of the benches that are part of the private property, which seems to confuse and annoy a lot of homeless folks looking for a place to camp out for the night. They were clearly pretty out of it, though I couldn't tell if it was natural issues, booze, or some kind of drugs, and it's always possible it was a good old mix-n-match situation for them. The older one of the pair was real chatty, wanted to tell me about his whole military career (supposedly he took part in both the Vietnam War and Gulf War, but he didn't look a day over 50 to me so I strongly doubt the first one) and what he thought of the Middle East and all the terrorists and so on, then he started telling me I should go into acting because I had a "presence" that he'd only ever seen from great actors. Meanwhile, the other guy was being mostly quiet and kinda walking around. I more or less causally adjusted how I was standing whenever he was moving off to one of my sides, because I'm not anywhere near stupid enough to let a homeless and possibly desperate dude get behind me and out of my sight. Chatty dude noticed it and commended me on my vigilance, told his bro to stop pacing around like a crazy person, and then continued to tell me about how I really needed to go to a place a few blocks away and take acting lessons. After about 15 minutes of talking with repeated hint drops and then blatant statements about how the dudes needed to leave, quiet guy got all butthurt and looked like he wanted to start some shit, but chatty guy had decided we were friends by that point and explained to his pal that I was just doing my job, that even though I surely wanted to let them stay (lol no) I could get fired if I did, blah blah blah. Basically he did my job for me as far as his friend was concerned, then they left. It was amusing, and it took up almost 20 minutes of my dull night, so that was nice.
Another time I found a guy in the parking garage with a shopping cart full of stuff strewn around a ~15 square foot area. He was using one of the electrical outlets to charge one of his cell phones (he had about a dozen of the things, likely stolen in the hopes of being able to sell them off). I told him he needed to gather his shit and get out, but he pleaded with me to let him charge up his phone a little more so he could call his mom. I would've told him to beat it immediately, but the only thing I can do is yell at people and threaten to call the cops and neither of those would make the dude pick up his stuff and leave any faster, so I took the smart route: I told him he could keep charging his phone, but only if he started picking up his stuff in the mean time. He did so, and as he did he decided it'd be a neat idea to ask me if I do drugs. Started off with weed, then asked about a bunch of other substances. Even after I told him I don't do any of it he asked if I had any he could buy from me, the silly bastard, but he eventually moved on to other questions. He asked if he could go through our lost and found and take stuff from it. Then he asked if I had any change. Then he asked if I had any spare food I could give him. Then he asked if I could get him something to drink. I said no to it all, of course, and he started getting irate. I reminded him about calling his mother, and that distracted him for a bit. He called her and told her he was coming over (it was about 4 AM at the time , by the way) and that she should make some coffee; she obviously told him no, so he got mad, then resorted to begging, then to whining. None of it seemed to work for him, so he hung up and just kinda sat there for a minute. I reminded him that it was time for him to fuck off, so he kept gathering his stuff while complaining at me. After a while he started demanding that I help him (haha no), then that I should get him some bags to pack his shit because he didn't have enough room for it all (dumbass got it all out of his shopping cart, he could get it all back in without extra storage, so nah), then that I needed to let him stay in the garage because his mom wouldn't let him come home (bitch please), and then that I needed to give him money/food/water or else I was basically condemning him to death on the streets (aw yiss, sweet sweet melodrama). I shot him down for it all, just like his mom did, and it took about 10 minutes for this idiot to gather all his stuff and start moving out. On the way by the parking attendant booth he tried to claim that the folding chair sitting outside of it on the curb thing just behind it (which is its permanent place for some reason, and I still don't understand how it hasn't been stolen) by saying it was his and that he brought it with him (despite the building name and "PARKING BOOTH" being written on it very obviously in black marker), and it took a couple minutes to get him to fuck off from that line of nonsense and finally off the property. He decided to go sit at the nearby bus stop and yell about pigs (because I guess private security guys can be called pigs too?) and how the country has gone to shit because poor innocent lads like himself are left to die on the streets and so on and so forth. I left him to it and went back into the building, and I checked 15 minutes later and he was nowhere near the building at all. I thought that was the end of the story, but the next day I found out that the day shift person found him on the property again at like 8 AM and ended up getting into a physical altercation with the dude, which of course led to a call to the police and the homeless dude getting carted away.