The Weirdest Things My Landlord Has Said

I’m not going to deny it, I have a strange living situation. My apartment is a two-bedroom unit of a house that sits almost directly under the train tracks. Neither room has a closet, but instead shares one walk-in closet that opens up into the living room. Also, the entire place is crooked, but, like, not even consistently crooked. The ceiling is crooked with the walls, the floor is crooked with the ceilings, and the whole place generally feels like an optical illusion. So yeah, it’s pretty weird. However, it’s also $1250 a month for a two-bedroom in Lakeview, making it, as far as I can tell, the best deal in all of Chicago. Possibly the world.

But, as you may have suspected from the title of this article, I’m not here to talk about my funky apartment. I’m here to talk about my funky landlord. From the day he made my roommate and I pay him a dollar as a symbolic gesture that we would rent the place (in lieu of a lease), to earlier this week when I exited my bathroom after a shower to see him and a contractor working on my (as far as I could tell, perfectly functioning) stove, he’s been consistent in his quirkiness. To give you a taste, here are the weirdest things he’s said in the last three years of me living there.

“And you can do…whatever you want…in this room.”

In this case, the words he said weren’t actually as weird as the way he said them. While showing the apartment to my roommate and I, he paused in front of a closed door, looked conspiratorially over at us (hungover, wearing gym shorts and t-shirts), and made the following statement in a low whisper. He then dramatically flung the door open to show us…a walk-in closet. Like I previously stated, this was the one closet in the apartment, so it would clearly need to be filled with our clothes. I don’t know what other possible use it could have, as it was lined with shelves and hanger bars, but clearly my landlord had some ideas. I’m not even sure why he called it a room, as it is, once again, very obviously a closet. We put our clothes in it. I don’t know.

“Just call me if you want to cook something.”

“Oh, was he trying to invite himself to a cookout at your apartment?” You may wonder. “That’s pretty weird.” No. No, that would have been weird, but preferable to the actual context, which is that this was his response to my roommate telling him that the stove wasn’t working. I wish I could tell you exactly what his answer meant, but at this point we’d learned that asking Tim more questions just got us further from our ultimate goal of having a working apartment. Was he saying he needed to be present to fix the stove every time we needed to cook? Was he offering to take us out to dinner instead of fixing our stove? I have no idea. My roommate replied with a simple text, saying “I want to cook something,” and our landlord came over and fixed the stove. If it works, don’t question it.

“That’s why I’m thinking about taking out the outside wall and putting in windows. Should take no more than three weeks. Your rooms will still be livable.”

Now, I know this may seem confusing for someone who doesn’t have a degree in translating my landlord, so I’ll break it down. First of all, this was said in a response to nothing. I know it sure seems like I said something to elicit this statement, but that’s just because all of Tim’s conversations start in the middle. This was his opening line to me when I opened the door to him knocking on a random Tuesday, and what he meant was, “I want to tear down the outside wall of your apartment, in the middle of November, and install floor-to-ceiling windows. Don’t worry, though, I won’t be tearing down the walls of your actual bedrooms. Is that cool?”

No. No, Tim, that’s not cool. For one, it’s 36 degrees outside. For two, I pay rent to be sheltered from the outdoors, not exposed to it. I wish that’s what I had said, but I know that Tim’s attention span isn’t that long, so I just replied with, “We like the living room how it is, but thanks.” I got a grunt in response, and he hasn’t torn down our apartment yet, so I’m cautiously counting it as a win.

“Yeah, the city is mad at me.”

This is never something you want to hear from the person whose job it is to make sure you have lodging in said city, but it’s even worse to hear in response to you texting them “Hey, why is the water shut off?” As usual, I never got any further information about this alleged beef with the fucking city of Chicago, but my water was turned back on a few hours later, so I guess Tim won.

“You want a full bathroom remodel? You’ll have to use buckets for about a week, but it’ll look real nice.”

At this point, I think we all realize that Tim actually hates his property, and wants nothing more than to tear it down and rebuild. And to be honest, I get it. It needs a fresh start. Unfortunately, I’m still living in it, and have been thwarting his every opportunity to demolish my apartment with my stupid needs like “showering” and “having a place to go to the bathroom.” This line was a response to me asking what had happened to the shower pressure, and if he could fix whatever he had done to make it go from feeling like a normal shower to a golden shower. I politely refused his offer of having me and my girlfriend shit in a bucket for a week while he remodeled our bathroom, and a few hours later my water pressure was back.

“Oh hey man. Gas should be working now.”

This happened just this week. I walked out of my bathroom in a towel, fresh from the shower, and noticed Tim and a contractor doing some kind of work on my stove. By now, I know that Tim just fucking loves to tinker with shit. I think it’s his release since I won’t let him fully rebuild the building. Or he just hates me. I can’t tell. Either way, this statement was concerning because a) the gas was working fine before, and b) after 3 years of dealing with Tim, I knew that while he loved tinkering with things, they never worked better after he “fixed” them. Unsurprisingly, when I came home that night, my apartment was filled with gas, and I had to stand outside in the freezing cold, airing out my place for a good half hour until it was livable. Classic Tim.

Is my landlord a psycho? Possibly. Is he a weird dude? Definitely. But he lets my pay my rent through Venmo and hasn’t raised prices in three years, so all in all, it could be a lot worse. My apartment may be crooked, but it’s home sweet home.


  1. My buddy and I rented a house from a guy on Craigslist one time. Decently nice guy but after googling him we found out he had been posted in one of the largest ecstasy busts when he tried to fly form Amsterdam to the US. Also he decided to turn the attic into 3 bedrooms, said it would take 2 months, took 8 months.


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