The Marketer Who's Rented in Brooklyn, Chicago, and Indiana
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The Marketer Who's Rented in Brooklyn, Chicago, and Indiana

Rental Histories
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If you’re like us here at Flip, you probably don’t have a lot to remember your last apartment by (other than a couple hundred dollars of the security deposit you never got back). That's what Rental Histories is for: a column to reminisce about the places you’ve temporarily called home.


Today on Rental Histories: Her first rental was a two-bedroom house in Indiana that cost $750 a month. Now this social media manager rents a one-bedroom apartment in Brooklyn for $1,700.

Occupation: Human Resources Assistant
Salary: $12.50 per hour
Moved In: August 2012
Moved Out: February 2013
Rental Type: 2 bed/1 bath house
Monthly Rent: $725 in total, $362.50 per person

Highlights: It was my first time living outside of my parent’s house—plus we had a garage and a yard.
Lowlights: My disgusting older boyfriend peed on my clothes when we broke up.

The first time my name appeared on a lease, I was 19 years old, returning to my hometown after dropping out of college. I’d attended college for one semester, stopped taking my antidepressants, then moved back to Indiana and into my mom’s house. I got a job as a human resources assistant for a company that hired contractors to clean grocery store floors in the middle of the night. I started dating a 27-year-old, and we decided to move in together.

We signed the lease for a two-bedroom house with a porch, a big yard, and a two-car detached garage in August 2012. The garage was a big bonus because my (then unbeknownst to me) evil boyfriend was into drifting. So we had three cars at the house at any given time: my car, his ‘daily’ car, and his shell of a Mazda RX-7 with a turbo in it.

I got two pet rats who were sisters and loved them very much. They had a huge cage in the living room. I kept the second bedroom as my room, which I assumed was the responsible thing to do. It was my first time living with a romantic partner, and I thought that if we got tired of being around each other, it could be nice to have separate spaces. That didn’t really work out. In February 2013 I found out he cheated on me, and when I confronted him about it, he exploded. He threw my laptop across the living room, destroying it. I hid in my room with the door shut, but the doors were cheap plywood, and he punched through it.

I paid him three months’ rent basically to use my room as a storage unit, and I left. In May 2013, I enlisted two guy friends I’d known since middle school to take me by the house and help me collect my things. My ex had urinated all over a box of my clothing and refused to let me take my pet rats with me. I cried a lot, collected my shit, and never saw him again. I forgot that the utilities were in my name and wouldn’t realize until I got a collections call five years later saying that I owed the electric company $42.

Occupation: Gelato scooper
Salary: $10 per hour
Moved In: July 2013
Moved Out: July 2014
Rental Type: 2 bed/1 bath apartment
Monthly Rent: $600 total, $300 per person

Highlights: I was happy to finally be living in Chicago, and the rent was extremely cheap.
Lowlights: My bedroom didn’t have a door, and I had to deal with the lack of a real heating system during the coldest winter I’d ever lived through.

In the summer of 2013, I decided to move to Chicago and found a friend of a friend through Facebook who was also looking for a roommate. I found an apartment in Pilsen and put in an application. Neither of us had jobs, so I wrote down my friends’ phone numbers and said they were our employers. The landlord never called to verify.

In retrospect, the 650-square-foot apartment was absolutely batshit. Even $300 in rent was too much. My “bedroom” —all 45 square feet of it—was big enough for a twin bed and pretty much nothing else. There was no door, so I hung a sheet up as a curtain. You had to walk through the second bedroom to get to the bathroom. The heat for the apartment came from a gas oven in the living room. I accidentally leaned against it once, and my skin blistered immediately. I have pictures of the inside of every place I’ve rented except this one. I was ashamed of it, but I did my best to make it feel like home.

I eventually got a job at a gelato shop. I didn’t make much money, but I could show up to work stoned and eat all the cashews out of the gelato with a sample spoon and get paid for it.

My roommate, A, was a really nice girl, and we got along. I found out that this was her first time living alone since rehab. She was going to meetings and staying sober, but she periodically relapsed. I got a new job writing news briefs about the restaurant industry for a consulting company, making $16 an hour. I started dating a guy and spent nine consecutive nights at his apartment. When I finally came back to my place, A was passed out, the floor littered with rotting delivery food and empty beer cans. She went home to Michigan and came back sober. But even when she was doing well, it was stressful to live there because I always felt like I was waiting for something bad to happen.

I published a book and got fired from my consulting company job because I barely did any work. My best friend decided to move to Chicago. He knew what living with A had been like, but needed a place fast and said he could take over my room until he found something. I moved out and he moved in.

Occupation: Office assistant, freelance writer, weed dealer
Salary: $13,000 per year
Moved In: July 2014
Moved Out: July 2015
Rental Type: 4 bed/1 bath duplex with a shared backyard
Monthly Rent: $1,245 total, $415 per person

Highlights: I had a giant bedroom, a backyard, roommates I got along with, and nice neighbors. Plus I was close to my favorite club.
Lowlights: I still wasn’t financially stable.

I moved into another apartment in Pilsen with two friends I’d made in Chicago. My bedroom was giant—twice the size of any bedroom I’d had before, with a walk-in closet and a weirdly low ceiling. I bought my first mattress bigger than a twin. Our landlord lived in the garden apartment, and we were his first-ever tenants. The week I moved in, he was throwing a party in the backyard where I gambled and smoked a joint with his friends.

I started traveling to promote my writing, getting paid to do readings and talks. I drove to the suburbs every month to buy ounces of weed for cheap and sell them. I also worked a few days a week for a few months as a “ticket reseller,” a job that entailed buying as many tickets to big concerts as possible using many, many credit cards. That didn’t feel good, morally, and I didn’t like making $9.50 an hour buying Celine Dion tickets for my rich boss to resell.

I wrote freelance for different websites and juggled a lot of other odd jobs in order to subsist—editing peoples’ resumes, writing papers for my friends who were in college, accepting money from people who didn’t have cars to help them move, etc. I ate a lot of bread, pasta, rice, and beans. I was on food stamps for a few months.

This was generally a happy living situation. My roommates and I got along, although they never cleaned much. My mom came to visit and there was so much mold growing on their dirty dishes in our sink that she insisted on putting on gloves and a face mask and soaking them in bleach before she washed them.

We lived two blocks away from the best party house I’ve ever been to—a DIY basement club that was disgusting and dirty and packed until 6 a.m. every weekend, until it eventually flooded with so much sewage that they couldn’t have DJs play there anymore.

I started dating a different guy who lived nearby. He took me on vacation with his family and, on the beach one night, told me he was falling in love with me. We became official and, a few months later, decided to move in together.

Occupation: Freelancer, weed dealer
Moved In: August 2015
Moved Out: August 2016
Salary: $17,000 per year
Rental Type: 2 bed/2 bath apartment
Monthly Rent: $1,300 total, $434 per person

Highlights: We had a jacuzzi tub, in-unit laundry, two balconies, central air, and enough space to host parties.
Lowlights: The apartment was completely isolated from everything, the opposite of walkable.

This apartment was the first "nice" place I ever lived in. It was in Lawndale, which was a pretty isolated part of town—there was only one store within walking distance, a liquor store that also sold canned food and single potatoes. My building was the newest one in the area, and a lot of the houses around it were boarded up. (For reference, the TV show Shameless was filmed nearby.)

My boyfriend and I shared the master bedroom, which was unparalleled in size. Our room had a private balcony overlooking the parking lot where I kept my car, a gigantic walk-in closet, and an ensuite bathroom with his and hers sinks, a giant jacuzzi tub, and a separate shower. We had a roommate, who lived in the other bedroom and had his own bathroom, too. The equally spacious living room came with its own balcony. We had a washer and dryer in the unit. We had central air. To me, the amenities were a fair trade for the isolated location.

With 1,200 square feet of apartment to fill, I needed more furniture. I traded a friend a copy of my book for her old IKEA couch. It was shitty but it worked—until someone sat on it too hard during our Friendsgiving dinner.

I found a regular freelance gig with Univision, the Spanish language TV channel. My job was to edit down episodes of TV shows—some ’80s classics, like Knight Rider and Miami Vice, plus a show called Airwolf about a secret, high-tech helicopter—to exactly 46 minutes and 10 seconds. I took a lot of joy in removing some of the segments in Knight Rider where David Hasselhoff’s character was aggressively pervy to women.

I also toured a lot while I lived there, accompanying my friends’ bands across the country and doing readings before their shows. My boyfriend and I broke up a week before our lease ended—the morning he was leaving to tour with his band for a full month. My mom came to town and helped me move out. I’ve never sweated more than I did that day, moving from one third-floor apartment to another in July. We disassembled my bed frame and threw it off the balcony because we didn’t want to carry it down the stairs, and it wouldn’t fit in my new room.

Occupation: Sandwich maker, creative writer
Salary: $20,000 per year
Moved In: August 2016
Moved Out: April 2017
Rental Type: 3 bed/1 bath apartment
Monthly Rent: $1,300 in total, $434 per person

Highlights: I loved my roommates, who gave me space when I needed it. I could watch the sunset from the apartment roof, and we were close to tons of coffee shops, bars, and restaurants.
Lowlights: I spent some of the saddest months of my adult life in this apartment.

I was extremely depressed when I moved to Humboldt Park. I was lucky that an old friend, R, had a room open when I needed one. The only way to fit my queen bed in the room and have space for any other furniture was to slide my mattress and box spring part way into the closet. It was a little like sleeping in a cave, which was fitting because I didn’t leave my bedroom until after dark every day for at least a month. I wrote freelance assignments on my computer in my room and occasionally emerged, in my robe, to make tea.

My roommates, R and T, were best friends. They were ideal roommates for this time in my life—they were a little bro-y and typically masculine in their reluctance to show emotions, which meant it felt very special when they popped their heads in my room to check up on me. They’d built a giant projector screen in the living room and, when I stopped being so sad about my breakup, I started watching a lot of Star Trek: The Next Generation. I invented a drinking game for the show and invited people over to play with me until we got blackout drunk. I developed a crush on a woman who worked at the coffee shop down the street, where I bought at least one croissant every day.

Eventually, I started working a few shifts at a sandwich shop to make some extra money. I got more reading gigs at colleges, including a few in the NYC area. I’d been visiting the city for writing-related stuff for about a year, and I started seeing a guy living there. In early November, at a concert, he put his arm around me and said, “Move here and be my girlfriend.” I was pretty sure I didn’t want to be his girlfriend—but I did start thinking about moving. As I was starting to realize, I’d been stagnating in Chicago for a long time.

I wasn’t on the lease, so I floated the idea to R and T. They weren’t thrilled that they’d have to find a new roommate so soon, but they understood. I started applying to any job I could find in New York. I flew there at the end of February and interviewed to be the receptionist at a hair salon, pretending I lived in the city already. The salon offered me the job.

I had a minor surgery scheduled for mid-March, so I told the salon I needed three weeks of rest before starting work. I had surgery in my hometown, spent two weeks recovering, then went back to my apartment to pack up my life. The last person I kissed in Chicago was my barista crush from the coffee shop. Three days before I left for New York, the stitches from my surgery broke open and I had to go to the ER. I pressed on. I packed all my stuff into a 10-foot U-Haul box truck and drove 13 hours to Brooklyn.

Occupation: Salon receptionist
Salary: $39,000 per year
Moved In: April 2017
Moved Out: July 2018
Rental Type: 4 bed/1 bath apartment
Monthly Rent: $2,800 total, $700 per person

Highlights: The apartment was incredibly cheap for East Williamsburg, and it was a good place to start my life in a new city.
Lowlights: Some of my roommates weren’t easy to live with. The apartment wasn’t residentially zoned and we didn’t have a written lease, which made it hard to get things fixed.

My first apartment in New York was not legally an apartment. The first and second floors of the building were a law office and a doctor’s office, and while the third floor had been renovated as an apartment, as far as I knew it was still zoned commercially. There was no written lease, as friends or friends of friends had been living there for seven years. The rent had never gone up during that time.

My first room in the apartment was on the small side, but I had a closet and the previous tenant had left his bed for me. The living space was huge—the apartment was 1,600 square feet in total—and we had roof access. No one cared if I sat by the window and smoked a cigarette every once and awhile. My roommates were all men over the age of 30, one of whom I knew a little. People left often enough that I had eight different roommates throughout my 15-month stay. I switched bedrooms three times, ending up in the biggest space in the apartment—bigger than my entire first apartment in Chicago. I had a walk-in closet, a queen bed, a couch, a coffee table, a desk, and a vanity to do my makeup.

Eventually, I got a job in social media—a big change from making $100 a day at the salon. I offered to pay $900 a month for the room, since it was significantly larger than the others and I had the money. The last roommate to move in while I was there, S, ended up being one of the biggest reasons for my departure. He was “crafty” and liked to bring random shit he found on the street home to tinker with. Once, while I was out of town, he’d disassembled my end table and another in the living room to combine them into one, very ugly, coffee table. He then painted it white, and—for some reason I couldn’t decipher—painted my rug white as well.

One week, I came home to find a nine-foot-long piece of Plexiglass stored in our narrow hallway. Another roommate told me S was planning to saw it into smaller pieces. I asked if he could do that outside, on our gigantic roof. He agreed—then posted pictures on social media of him sawing it inside, covering the living room in Plexiglass dust. We argued over text, he insulted me, refused to take accountability, and said I was only mad because I had “issues with male authority figures.”

That night, I stayed awake until 2 a.m. scheduling apartment viewings. The next day, I visited four one-bedrooms that cost less than $2,000 a month and put down a deposit on one on the spot.

Occupation: Social media manager
Salary: $80,000 per year
Moved In: July 2018
Rental Type: 1 bed/1 bath apartment
Monthly Rent: $1,700

Highlights: I love the neighborhood. Being able to afford this place on my own makes me feel like a success.
Lowlights: It’s my first time paying this much rent, and there’s still no outdoor space. Living alone took a lot of getting used to.

Greenpoint had long been my favorite neighborhood in Brooklyn—it’s where I stayed with friends when I visited from Chicago, and I remember thinking, “I could never afford to live here.” But I’d been working at my first “real” job for a year, and I was ready to live alone.

If you had told me in 2013—or even 2017—that I would be spending $1,700 a month on rent, I probably would have spit in your face for insulting me. With the broker’s fee and security deposit and first month’s rent, it cost more than $5,000 to move in. Still, the apartment is astonishingly affordable for the area.

I moved in and slowly started arranging things to be exactly how I wanted them. The apartment is on the first floor, so I put frosted window stickers up to maximize privacy and natural light. The bathtub is small, but it’s the only apartment in my budget I found that had a bathtub at all. (And I’m short, so I still fit.) The bedroom is huge, so I hung up a long curtain to separate my sleeping area from my living space. I bought my first real couch. I have five bicycles mounted on the walls and ceilings to give me as much floor space as possible, and there are eight built-in closets, so I didn’t have to buy a lot of shelving or dressers.

Living alone was a bit of an adjustment. Although I’d butted heads with several of my roommates in the Williamsburg apartment, I got along with a few of them. I missed coming home from work and having someone to chat with. I missed cooking for more than one person (when I did cook, which was rare). I also had to change how I spent my money to adjust to the monthly rent. When I re-signed the lease, I was fully prepared to negotiate a huge rent increase. I assumed my landlord had got me on the hook with a great deal and was planning to increase the rent by at least $300, which would have been justifiable. Turns out, my rent only increased by $50.

I’m happy here! It feels like home. I think I’d like my next place to have a bigger bathroom and some kind of outdoor space—but my lease isn’t up for another year, and I’m happy to stay.


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