From Random Roommates to Best Friends: 4 Stories

Cassandra Cloutier

By Cassandra Cloutier

Dec 06, 2023

If you’ve ever had to move quickly on a small budget or to a new city on your own, you’ve likely navigated the unpredictable world of random roommate situations. For these renters, though, their good roommates turned into some of their closest friendships. They shared their stories with ApartmentAdvisor.

How These Random Roommates Went From Strangers to Second Families

Seeking inspiration as you begin your roommate search? Here's four stories of New York City roommates who went from strangers to best friends in just a few weeks.

Sarah S. & Starsha S.

Sarah needed to get away from a crazy boyfriend she’d been living with and was looking for a new roommate. She wasn’t expecting to find a close friend.

The Craigslist apartment she found on the Upper East Side in New York was close to the lap pool she frequented, cheap, and available. She paid $800 a month for a glorified closet with a lofted bed in a two-bedroom apartment she shared with three roommates.

One day, Sarah came home with a bottle of red wine in one hand and a bottle of prosecco in the other. Fourteen years later, Sarah says, she and her then roommate Starsha think of it as the late night that their friendship began.

“From that moment, we were soulmates forever.” 

The incredibly clean Starsha managed the chore schedule, while Sarah just contained her mess to her bedroom. Neither had a serious partner at the time, so they bonded over the “I went on this awful date with this awful person” discourse of dating, Sarah says.

After their year and a half as roommates, they made it a priority to stay in touch. During COVID, they committed to monthly Zoom check-ins from their respective states. Now, they connect over jobs and various family dramas, each conversation picking up like no time has passed. 

“I met my best friend on Craigslist,” Sarah laughs. “It’s this long-term, ongoing relationship that has evolved throughout the years.”

Alexandra O. & Kerrie S.

Alexandra advertised her “cozy” East Harlem, NY apartment on Craigslist every few months. Her spare room was a revolving door for medical professionals at Mount Sinai — a living situation that prioritized convenience over making friends. Until she found her roommate Kerrie.

Their first real memory together was a Yankees game they attended in 2012. At the game, they planned a beach trip for the following day and shook on it. The next morning, they each waited for the other to bail.

“We were both tired and a little bit hungover, but we got up and got our bagels,” Alexandra remembers. “And then we just loved each other. That was it.”

The beginning of their platonic love story was memorialized by matching “I heart mustache” sweatshirts they bought, adorned with red hearts and glittery gold mustaches.

(Left) Kerrie and Alexandra at home. (Right, top) Kerrie in the "I heart mustache" sweatshirt that started it all. (Right, bottom) Kerrie with Alexandra's dog, Kiya. Photos courtesy of Alexandra.(Left) Kerrie and Alexandra at home. (Right, top) Kerrie in the "I heart mustache" sweatshirt that started it all. (Right, bottom) Kerrie with Alexandra's dog, Kiya. Photos courtesy of Alexandra.

Over the next two years, they shared food — Kerrie taught Alexandra the joy of snacking — drinks and presents. One Easter, Kerrie prepared “baskets” out of mixed six packs of beer, complete with decorative pastel grass. They also tag-teamed on care for Alexandra’s dog, Kiya. Alexandra would often come home to find Kerrie studying and cuddling the beloved Pitbull on the couch. 

Alexandra admired how Kerrie chose to do things that elevated her experience of each day, from adding salsa to her famous breakfast sandwiches to turning the process of getting ready for a night out into a wine and music fueled event.

“She taught me how to be with myself in a cool way,” Alexandra says.

Kerrie eventually moved out to live with her boyfriend, but Alexandra jokes that they could have lived together forever.

James G. & Ximena V.

James made sure a few friends knew where he was going before venturing from Manhattan to Weehawken, NJ in 2012. A Craigslist inquiry led him to an apartment so slanted you could lift your feet in a rolling chair and sail from one end to the other, but the rent was $466 a month.

Ximena was already living in the apartment and the two bonded over rolling their eyes at a third roommate — a musician working on a production of “Silence! The Musical,” who sang off-key and frequently fell asleep shirtless on their shared couch.

When he moved out, Ximena and James became even closer.

“From then on, it was James and I accepting people into the living space,” Ximena says. “We were looking for a family member.”

The self-described “parents of the apartment,” they were the ones convening occasional family meetings over issues ranging from cleanliness with different roommates to one tenant’s loud sleepovers that could be heard throughout the space.

They know each other better than they know most people, they agree, having seen one another in the mornings before either of them is speaking yet.

“You don’t see a lot of your friends like that.” James says.

“I feel comfortable showing up as I am.” Ximena adds. “However it is that I am.”

Emily M. & Brandon R.

Emily knew she was going to be friends with her random roommate Brandon the first time she asked him to kill a cockroach.

“I’m a Buddhist,” he reasoned.

“Touché,” she remembers thinking. “It was a power move.”

Early in the COVID pandemic, a broker in a Facebook renters’ group connected them and a third roommate, who kept waiting for her office to reopen and paid rent for an entire year without moving in.

Because of the pandemic, they were home 24/7.

“The pleasantries of the typical roommate etiquette were out the door,” Emily explains. 

As it was 2020, there were endless social and political events to talk about and John Mulaney specials for them to watch together. She also started fostering dogs, so they spent a lot of their time strolling with the temporary pets.

According to Emily, they are compatible as roommates because they’re both very communicative and direct. If something is bothering one of them, they ask to work on it.

Emily (center) and Brandon (right) on a rooftop. Photo courtesy of Emily.Emily (center) and Brandon (right) on a rooftop. Photo courtesy of Emily.

“It doesn’t really fester,” she says.

They’ve lived in two more places together along with a third roommate they met on their roof during that first year of the COVID pandemic.

Once they were good friends, Emily asked Brandon if he could’ve actually killed the cockroach.

“Absolutely,” he said. “But I didn’t think we’d be friends.”

Want to find the perfect roommate? Here’s how.

If you are hoping to become besties with your roommate, we have a few tips for how to start off on the right foot.

First things first, you’ll want to vet any potential roommates before move-in day to make sure you will be compatible. If you are thinking of living with someone, ask them a few screening questions to see how similar your lifestyles are. Examples include:

  • Do you keep your common living space neat and tidy, or are you fine with a little clutter and mess?
  • Do you like to host social gatherings in your apartment, or do you prefer to socialize elsewhere?
  • Are you a morning person or a night owl?

If you’ve found someone you have a good feeling about but are worried about potential conflict arising, you can also write out a roommate agreement during the first couple of weeks of living together. Like a contract for roommates, these types of agreements include clauses on division of responsibilities (like who pays for which utilities), cleaning duties, tolerance for live-in pets and four-legged visitors, and quiet hours, to name a few.

Finally, if you have yet to live on your own or have a bad track record with roommates, you may be struggling to figure out what type of person you’d actually live best with — even if you are prepared with your screening question. This is where our Roommate Compatibility Test can help. Whether you’re an incoming freshman hoping to pick the perfect first college roommate or a young adult seeking to avoid co-living headaches, this free and fast roommate survey tells you what kind of roommate you are — and what kind you’d live best with. It takes less than 5 minutes and requires no sign up.

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