4 readers reveal how money ruined a friendship—from bill-splitting to “borrowing”

There’s an old American proverb that says, “Before borrowing money from a friend, decide which you need most.” While we would like to think that nothing can come between two friends, very often mixing money and friendship together is akin to mixing oil and water—sometimes it just doesn’t work. Sadly, it’s all too common when the matter of cash comes between friends, the friendship either dissipates completely or is never the same again.

We asked some people to share their experiences with how money ruined their friendship while also checking in with relationship and financial experts as to how they might have handled things differently. While every money and friendship situation is different, as there are many reasons why people build certain relationships with money, it’s never a bad idea to learn how we can have better conversations about money—without judgment.

The Extreme Bill Splitter

“I’m very much in support of bill splitting but I had a friend who always took it to the extreme. Anytime we went out, he always used to insist that not only do we split the bill to the last cent but we should also split by ratio. He hated it when he had to cover even a few cents for anyone.

It reached the height one day when I received a Venmo request from him that I pay for the straw that I ordered for during our last hangout together. We had already split the total into two. But he had gone home to recalculate our individual expenses and discovered the straw cost a few extra cents. I refused to oblige because there had been a number of occasions when we had split bills in two but he had actually spent more. He made such a big deal of this that we got into a verbal fight. We never really got back our friendship because of the things that were said that day.” – Joe Flanagan, Engineer.

In this situation, Nicole Sbordone, LCSW, and author of Surviving Female Friendships: The Good, The Bad, and The Ugly, says if this person is a close friend, you might want to consider seeking compassion and curiosity. “On one hand, I understand wanting to be fair when it comes to splitting the bill,” she says. “However, on the other hand, when the person seems extreme (as in this example), there may need to be a conversation between the friends as to why this is so important to the person. I find when people talk about what’s actually going on underneath their actions, it can lead to a very positive and helpful conversation. Maybe he has been taken advantage of in the past and has become rigid but doesn’t see it? Maybe he’s struggling with money? It’s helpful to talk about what’s going on.”

Derek Hagen, financial therapist and financial planner, agrees that a conversation would have been helpful in this scenario. “Most people are accommodating if they learn that something they are doing is hurting or frustrating you. In this case, the lack of talking about it meant there were likely some repressed feelings that came out all at once. These situations are not productive. We are stressed out and more likely to say things we don’t mean, or in ways that are aggressive.” Hagen says that if these two friends had talked it out and had arrived on the same page, they could’ve found solutions that would have worked for both, including separate checks, or eating at restaurants where you need to pay separately at a counter.

The Stingy Roommate

“I had a roommate who was really weird about money. She’d hold people to every penny, even though everyone else was much flexible (like one person would pay for [toilet paper] and then another would). But yet, sometimes she’d go out and buy things, like decorations, and then bill people for their share, even though no one else had agreed to the purchases. She was so precious about money that she once genuinely suggested that we charged guests to shower, and tried to make the rest of us shave our legs with no water to save money, though she had more money than the rest of us.

Fortunately, one of my roommates pushed back and did it in such a jokey way that she just dealt with it. But she’d still do weird stuff, like leave passive aggressive signs on appliances to make people use less amenities, even though we were all pretty conscious about that stuff, anyway.” – Chloe,* a writer.

When it comes to living with roommates, Sbordone says it’s important to sit down and talk about expectations about living together, including compromising on how you all utilize the utilities. “If someone is constantly cold, while the other is hot, try meeting in the middle,” she says. “The important piece is to talk about it. If you’ve tried talking about it, and the person is just not budging, then I suggest looking for a different roommate. No one should feel uncomfortable where they live.”

For her part, Chloe says she’s no longer friends with this person and she’s learned to “live with people who have similar values to [her]. It’s not worth being in constant battles about whether you can run water in your own home.”

The Out-of-Money Healer

“An energy healer was referred to me by a former close friend. She seemed so happy and clear on her path. I asked her how she got to this place of bliss and she told me that she worked with this woman who did her readings and helped her find true love. Perfect commercial, right? At the time I was totally scattered and desperate for things to settle down inside of my soul.

The first time I met the healer, she was incredible. The reading was really compelling; she knew details about my family down to what my sister-in-law did for a living. I was sold. I bought a package of sessions. As I started seeing her more she started inserting herself in my life and made me part of her friend circle. Slowly but surely, the asks started coming: ‘Can you advance me for your next sessions because (I can’t pay rent, feed cats, etc).’ I felt accountable to her at this point. She knew everything about me (so I thought). Then the blatant money asks began and she would promise she would pay me back within a week, ‘I’m just waiting for this payment or that income to hit my account.’

When I would circle back a week later for repayment, her reply was, ‘Oh, sure. I could also just credit you for two sessions. I think we’re really close to a breakthrough—think about it.’ This happened another time and eventually, she asked me (a single mom working [with] two jobs) to drive my truck down to Beverly Hills to pick up some antique table she found on Craigslist. ‘They need cash. Can you go give them cash, pick it up and drop it off to me? I’ll pay you back when you get here.’ That was the first time I said no. I don’t know why I went back to her after that but I did and the reading was so clearly not for me.

I later found out from the friend who recommended her that she also asked her for $400 [but later the check bounced]. After weeks of trying to convince her that this ‘healer’ was a vampire and preying on people who need help or guidance, I realized she was not going to listen to me. I blocked the healer from all contact and the friend eventually disappeared from my life too.” – Karen,* a marketing specialist.

Hagen says when it comes to money, communication is key. “In this case, the moment it was getting uncomfortable is when it made sense to request a conversation. We should trust our gut instincts. Meaning, it probably felt weird to have someone new start asking for things. That’s the alarm,” he says. “Just because there’s an alarm, though, doesn’t mean anything is necessarily wrong. That’s why it’s helpful to have a conversation and get on the same page. That way the healer friend knows where you sit and what your comfort zones are.”

Similarly, Sbordone says when it comes to asking for favors, including money, setting boundaries is crucial. “When we start to feel taken advantage of, it’s super important to set boundaries and say no,” she says. “I can’t tell you how many times I work with clients on saying no and that it’s okay to do.” During situations like these, it’s important to ask yourself why this may be happening in the first place and how you can prevent this in the future. “We need to work on healthy boundaries in any type of relationship,” says Sbordone.

The Excessive Borrower

“I was a swimmer for most of my life and that meant, literally, having little to no social life. The people that I knew were my family, a few acquaintances from school, and most prominently, my coach and teammates. I had one teammate who I was really close to. Our friendship lasted a good five years—however, I realized that our friendship only lasted that long because I was very generous towards him.

It started with the small things, and take note, we were just teens at that time. It started out with giving him extra money when he was short when we were buying soda or something. He said he would pay me back, but at that time it was only around $2, so I just shrugged it off and said don’t worry about it. I regret saying that.

When we got older, it started to escalate. I started lending him money for gas, for dinner, he often stayed at my place—crashed, rather. It was getting alarming since I didn’t know how to tell him, “Maybe you want to pay me back?” His family was loaded. And I mean loaded. Yet, it was like I was supporting him for food, swimming trunks, almost everything!

The worst, and probably the tipping point as to how our friendship ended, was when he was impressing some girl back in high school. Guess what? He wanted me to buy flowers for her. I repeat: He wanted me to spend MY OWN MONEY to impress some girl. I got pissed and I asked him bluntly, when are you gonna pay me back? He was shocked, because I never asked him to pay me back. Then he started acting as if HE’S ENTITLED and that I should pay. Needless to say, it didn’t end well. I haven’t spoken to him in ten years.” – Rick Patterson, founder of Poolonomics.

Again, having clear communication and setting boundaries is key, says Sbordone. “If you never say anything, the person will continue to do what they’re doing because they think it’s okay. We don’t realize that we enable behavior by staying silent, even though we may be seething inside. If this person could do this all over again, they could have spoken up right away and asked when the other person would pay them back. I suggest we be clear and speak up sooner than later to avoid what happened in this story.”

So is lending money to friends ever a good idea?

Sbordone says that it depends on the nature of the friendship: “A long-time friend versus a friend you’re only had for a few months or someone reliable versus someone flaky and not reliable,” she says, while also having a written agreement about how the money will be paid back. In the end, if you don’t want to risk losing your friendship over money, it all comes down to having those tough conversations.

“The common thread running through all four scenarios is that money conversations are hard, uncomfortable, and awkward, especially when we’re denying a request,” says Hagen. “When we have to say ‘no’ it brings up a second awkward conversation taboo—confrontation. If we can learn to have better money conversations, then many of our frustrating situations with our friends would be mitigated.”