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The Bushwick one-bedroom seemed perfect for Henry and his fiancé — a renovated unit in a charming prewar building that even had an in-unit washer-dryer. It rented for $3,000 — “New York expensive,” per Henry, but cheap in the frenzy of of the 2023 rental market. Plus, there were no other prospective renters to fend off in a bidding war and no broker fee. He got the place through his friend Reid, who had bought the condo before having a baby and was looking for a tenant to take it over. He asked Henry for a month’s rent as a deposit. As for a lease, Reid didn’t want to go through the hassle of notifying his building about having a renter. And Henry didn’t care. “I figured we would work it out like two dudes,” he said.

What that became, in practice, was closer to psychic warfare. “We both tried to leverage the fact that we’re supposed to be friends,” Henry said. “I’d use it against him all the time: ‘Come on, dude, what are you talking about?’ And he’d do the same thing to me.” Take, for example, the time Henry and his fiancé fostered a dog without asking Reid first: “I was like, ‘He is not going to evict us for having a dog.’” Reid didn’t, but he also didn’t find out about the dog until he inspected the place after Henry moved out. Since there was dog-related damage, Reid announced he was keeping the entire security deposit. Henry haggled him down. (They agreed to $900 over claw marks on a door.) “We both got away with taking advantage of the situation,” said Henry, who was still surprised at his friend’s reaction when he broke the news that he was leaving New York. “I felt bad telling him,” Henry said. “But he was like, ‘Nice. That sounds great. I’m going to charge someone else way more for this.’”

There’s an obvious appeal to the idea of renting from a friend in this market. A friend’s place tends to be nicer, maybe because they themselves lived there and are subletting, or because they bought the building and are living upstairs, or because they’d be ashamed to offer anything too grim. But the truth of the arrangement can be more complicated. What comes first: the friendship or the rental agreement? When a building is too friendly, where are the boundaries? And who’s going to enforce them? A text about a leaky sink may get ignored; we’re friends, after all. Or worse, it may end up on a list of private resentments. Who is she to complain about a leak? Who is he not to fix it?

Still, some real estate seems too good to pass up. “I was optimistic,” said Ida of the townhouse in a celebrity-stuffed section of Brownstone Brooklyn that her longtime friend offered as a cheap rental. (Like most names in this piece, Ida is a pseudonym.) The fantasy started as a favor. In 2020, after her friends — let’s call them Clara and Brett — absconded to a country house during the early pandemic, they asked Ida and her husband to be on call if they ever had an issue at the Brooklyn house. When it was clear the couple wasn’t coming back anytime soon, Ida and Pete asked if they could move in. Clara and Brett agreed and set a rent that was cheaper than the couple’s old one-bedroom. There was one crucial caveat, though: Clara and Brett wanted to be able to visit for the occasional weekend. That seemed easy enough since Ida and Pete could just stay in one of the many bedrooms. So they agreed, asking Clara and Brett only to give them a month’s notice for their visits. At first, the whole thing was a dream: There was finally enough space to work from home, and the place was quieter than Ida and Pete’s previous apartment. When Ida’s family visited, they didn’t have to pay for hotels. And Clara and Brett’s first visit was fun, especially in the “bubble” days of COVID when any socializing seemed thrilling. But soon, Brett and Clara stopped giving long lead times. They apologized but kept showing up without much notice and with an attitude Ida described as “Well, it’s our house.’” The friendship that had made the arrangement seem fun and breezy was now causing extra stress. It came to a head when they got a message from Clara and Brett announcing a new house rule — a change made during yet another unannounced visit. Ida knew it was time to move. “I wanted to end it before it got really bad,” she said.

“I got a total complex,” said June, who in 2018 rented to a friend who needed a place after a breakup. “I started losing my mental well-being, thinking everyone hated me.” She and her husband had just sunk their life savings into a brownstone with a downstairs unit — an apartment they had quite happily lived in themselves while they were fixing the upstairs. And who better to take it than her friend Ruby? She was fun, had a great job, and could make June laugh. “I had this image in my head of renting to a friend you could have dinners with,” she said. She offered below market rent, backyard access, and laundry and even volunteered to watch Ruby’s cat when Ruby went out of town. But it was “not a luxury building,” June said. “It’s 150 years old.” This might have been clear to anyone who had ever lived in a brownstone, but Ruby seemed to have higher expectations and got upset when there was an issue with, say, the hot water or the sound of footsteps overhead. June, who felt awful about disappointing a friend, would try to make amends. “I even left her flowers once,” she said. For fixes other tenants would normally make themselves, like changing a lightbulb, Ruby would call down June’s husband to act as a handyman. He didn’t mind. He even installed security cameras after Ruby said she felt threatened by workers repairing the façade, who had a view through her windows. But nothing ever seemed to be enough. The breaking point came during a trip June and her husband took upstate to go apple picking with their kids. Ruby, who was back home, called to tell her the workers outside were upsetting her. Then she started posting a series of videos on social media complaining about her living situation. This time, it was June who felt violated. They had friends in common. “I started getting paranoid that everyone, all of our friends, hated me,” said June. Ruby eventually moved out.

I talked to broker Mark Jovanovic about why renting to friends can be so perilous. (He would know, after all — he had helped install tenants in a converted mansion on the Upper West Side whose owners had initially rented to friends and colleagues.) “I’ve never seen someone rent to their friends at the highest possible rent,” he said. But the friend discount can have unspoken expectations attached: “Most of the time the friend is paying a better rate, but the landlord’s attitude is ‘I’m giving you a discount because I don’t want to deal with the small problems.’” Then those small problems create larger ones.

Even when a friend becomes an ideal landlord, it can put their tenant friends in an awkward spot. Are they now the ones taking advantage? Nancy Silverman rented a one-bedroom in Astoria from a friend who had inherited the building. But the friend was “not someone who felt comfortable being a landlord. It was ideologically conflicting for her,” Nancy said. The friend didn’t raise the rent, despite making improvements to the building, and Nancy found herself, in a sense, reverse landlording: She encouraged her friend to raise the rent, then effectively raised her own rent, just so she didn’t feel like a cheat. Nancy ultimately opted to move out since it was clear this dynamic would persist. Perhaps it would free her friend to be a landlord to someone who might be more “tenant-y,” she said. I almost waded into this situation myself when a close friend offered me a one-bedroom in the garden level of her Bed-Stuy townhouse. My friend was the definition of a reluctant landlord — an anti-Establishment type who furnished her grad-school hovel with wine crates and avoided any talk of money. If I said “yes,” would I seem like an entitled loser if I complained about a broken toilet? Besides, our friendship thrived on infrequent run-ins. We could tell hourlong catch-up stories in dive bars because we weren’t constantly running into each other and forcing soulless small talk. I decided we were better off as friends than as partners in the business of paying off her mortgage.

But sometimes a new shared interest in hardwood floors and package theft can enliven an old friendship. “I think I was a little afraid it would make things awkward in our relationship,” said Danielle, a 30-something who preferred to go by her first name only. Her friend had bought and restored a three-unit building in Ridgewood, moved into the top floor, and brought in friends to take over the two units below. He had renovated the place himself — resisting the glossy white paint and Home Depot cabinetry of corporate landlords in favor of original hardwood and vibrant colors like a turquoise kitchen with butter-yellow cabinets. Even so, Danielle added, “Nothing is perfect.” Those lovely hardwood floors gave her months of splinters because of a skipped step when they were restored. Not that she bugged him after the first one came loose. “It’s sometimes a little more awkward to ask for things to get repaired,” she admitted. But there’s also a silver lining. When they do start talking about an issue, she learns about the cost of materials and the required tools, and she gets a window into what her friend’s life is like as a landlord. Often, she will stay to help with the fix or just to chat. Afterward they might get a beer. And now, they’re meeting every month or so to play Dungeons & Dragons, led by the landlord’s friend on the first floor. Before Danielle moved in, they didn’t get together all that often. Today, she said, “I’d say it’s made us closer.”

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