Nicole, 23

“Every month, my friend and I discuss whether we should stick around our hometown and do the same thing every weekend (ex., go to a local club) or prepare for one big weekend trip (ex., Disney World), even if that means staying in occasionally so we can save up.

“Personally, I prefer saving up for a vacation because I love exploring new places and enjoy road trips and plane rides while also getting a chance to relax in between. My friend, however, never really wants to get out of her comfort zone to try new things and would rather spend money every weekend at nearby bars and restaurants. I’m getting a little exhausted of her lifestyle and spending habits, but I don’t know how to tell her.”

What an expert suggests you do:

According to Franco, psychologist and friendship expert, having a conversation about compromise is a good start in this situation. “Maybe this means Nicole goes to a club for only a few hours or only gets one drink some nights or her friend spends some nights in with her hanging out so they’re able to go on the trips she wants,” she suggests.

“However, I’d also remember that one friend doesn’t have to be everything for you,” Franco adds. “Of course, you can take turns going out or going on trips together, but it’s good to also find other friends who can more regularly do your weekend trips with you.”

Caitlin, 26

“I have a typical 10-6 job; my friends are freelancers, so their schedules vary. Oftentimes, they’ll be hard at work for a few weeks at a time, then want to go away on long vacations with multiple events and excursions throughout the day — but I don’t have that kind of flexibility, nor do I get my paychecks in large sums.

“Our timing and financial availabilities are so different, which usually results in someone (aka me) missing out on important moments because these trips keep getting planned around when my friends get their time off and big checks. Guess I’ll just have to keep living with FOMO.”

What an expert suggests you do:

A good initial step in this situation is to have an open conversation with friends about availability, but Franco says Caitlin should also take the initiative to plan trips herself. “Instead of relying on friends to plan trips around her schedule, she should be making plans of her own and inviting them,” suggests Franco, adding, “If her freelancer friends are only really able to take these vacations during those times because of their financial constraints/schedule, then she might want to look for friends who have a similar work schedule as her to go on trips with.”

Franco believes that this might also help Caitlin reframe her feelings of FOMO. “By focusing on her own needs and going on vacations when she’s able to, Caitlin will be able to feel happy for her friends when they go on trips instead of focusing on what she’s missing out on,” she says.

Brittany, 24

“When I was 16, my friend invited me down to her family’s condo for the week so we could go to an amusement park that we had free tickets to. I was very grateful that her mom let me stay with them, and I even offered to pay them or bring food, but her mom insisted that I keep my money. My friend had other thoughts.

“When we were at the amusement park, she ‘forgot her wallet’ so I had to pay for everything. She promised me she was going to pay me back when we got back, but never did. The next day, the same thing happened. When I told her that I couldn’t keep paying for her, she responded, ‘Well, we are hosting you here for free, so the least you can do is pay a little bit.’

“The last day of the trip, I asked her to pay me back at least for her souvenirs and her pictures. She said she didn't have any cash and made her dad pay me back. When she took the money out of her dad's account, she shorted me at least $20. Needless to say, we weren’t friends for much longer.”

What an expert suggests you do:

According to licensed counselor Degges-White, Brittany could have better handled the situation by setting some boundaries earlier on and keeping tabs moving forward. “Brittany couldn’t have initially known that her friend was not to be trusted when it came to money on that first day,” says Degges-White. “But she could have perhaps set some clear limits on how much money she had available to spend for the day and checked with her friend that she had her wallet before leaving the house the next morning.”

Unless they had agreed beforehand that Brittany would make up the cost of her friend’s family paying for her lodging and food by paying for her friend’s food and souvenirs at the park, asking to be paid back was the right thing to do, however uncomfortable it felt in the moment.

Shelby, 29

“I had a nightmare roommate a few years ago. The day we moved in, she mentioned offhandedly that she wanted to split a rug and a coffee table. We were basically strangers at this point, but I wanted to eventually be friends, [so] I told her as nicely as possible that it wasn't in my budget at the moment, thinking we could have another convo in the next few weeks.

“A few days later, I saw she had bought a bunch of new stuff (a rug, a coffee table, and large shelving unit) for the living room. I thought she just didn't want to wait for me and had bought it herself, but a few days later, she texted me and asked when I could pay her back for my ‘half’ of all the new stuff, which amounted to a little over $250.

“Months later, when I caught on to all the things she was doing to me financially (like collecting my ‘half’ of bills then not paying them), I realized she’d overcharged me for the Ikea furniture. When I confronted her, she made up a story about buying it all from Craigslist and having to get a U-Haul to pick everything up. No comment from her when I pointed out the Ikea toolset and instruction booklet that had sat on one of the shelves of the unit for months after she bought it.”

What an expert suggests you do:

According to Degges-White, the best way to handle this situation would be to pay attention to initial warning signs and act accordingly. “While you can’t undo what happened in the past, it’s a lesson [learned] that if you’re splitting bills with anyone, everyone needs to see the original bill and the receipt to show that the expense was actually paid by the person collecting the money,” she suggests. “If someone tries to take advantage of you once, there’s a chance they’ll try to take advantage of you again.”

If you have reason to believe money from shared expenses might not end up in the right hands, Degges-White suggests volunteering to oversee the transaction and collecting and paying the debt yourself.

Hannah*, 29

“I was fortunate enough to not have to worry about money until I graduated. In college, the only convenient grocery store was Whole Foods, so I falsely assumed that those prices were normal.

“Once I started making my own (small) salary, I was amazed that prices were so much cheaper at other grocery stores. I vividly remember a conversation with one of my good friends at the time where I shared my amazement that chicken breast doesn’t have to cost $14 a pound. She got annoyed by my reaction and called out my privilege for being able to drop money at Whole Foods up until that point.

“After that, things got tense and our friendship never recovered. I look back on that conversation now, and realize that I could have handled it better and should have checked my privilege.”

What an expert suggests you do:

Franco says the best way to approach this situation is by being vulnerable and admitting when you’re in the wrong. “If this is a friendship you’d want to rekindle, you could go to your friend and tell her, ‘Hey, I now realize that my viewpoint on finances was not in line with the majority of the population, and I’m sorry I was unintentionally insensitive when coming to terms with that discovery,’” Franco suggests. Approaching the situation by empathizing with her friend, listening, and being open about where she went wrong could probably heal the rift in this friendship.

Prince, 24

“I was a freshman in college when I received some money from my sister. This was a big deal because I was broke at the time and was excited to have money for food and other school expenses. My friend was with me when I got the alert, and he asked me if he could borrow some money.

“Though I declined at first, he pleaded and promised to pay me back the next week. After much pressure, I gave in. However, the following week, I realized he had been avoiding me and wouldn’t come to my room or answer his phone when I called; I couldn’t find him anywhere.

“A month later, I saw him with five guys and asked him for my money. He denied that he’d ever borrowed any, and the situation escalated as his new friends backed him up. Faced with the certainty of a fight I couldn’t win, I chose to walk away. We lost communication after that, and we are no longer friends.”

What an expert suggests you do:

You should always avoid loaning money to a friend unless you are willing to think of it as a gift, according to Degges-White. “Money is a resource that is super liquid, and once it’s been spent, it’s not going to be easy to recover if a friend was short on cash from the outset,” she says. “Ideally, we only allow ourselves to get burned like this one time as we learn that money changes relationships in unpredictable ways.”

Teddi, 26

“My bestie and I do almost everything together, and usually I'm the one who puts my credit card down for drinks, food, taxis, etc. Rather than constantly Venmo request her each time, I request lump sums — which can be hundreds of dollars after everything is added up — from her every couple weeks. But then she gets annoyed when she sees the total, even though it's all stuff she wanted or participated in at the time.

“It’d be one thing if she offered to drop down her own credit card, but she never does. Maybe it’s best to keep everything separate moving forward.”

What an expert suggests you do:

According to Degges-White, Teddi’s idea of separate checks might be her best option moving forward unless she’s willing to send Venmos for each night out. “For some of us, it’s easier to manage spending smaller sums of money on these items versus one big lump sum every couple of weeks,” she explains. “For instance, if I see that I’m getting too close to the zero balance in my checking account, I can stop going out.”

However, if someone is allowed to “coast” for a while due to a friend’s willingness to float them the funds, it can be stressful to receive a big bill and realize your bank balance is too low to easily cover the Venmo loan and other expenses. “Teddi has two choices: either send Venmos for each night out or refuse to cover her bestie’s drinks,” Degges-White says.

Jessica, 23

“My roommate and I were freshmen living in the same suite as a senior, so I had already expected us to butt heads because of our age gap. But the first few weeks were actually nice; we hung out, we got along — I would say we were all friends.

“Then came our first trip to the grocery store together. My roommate drove, we all picked items we wanted, and I put everything on my credit card. The next time, I drove, we all picked items we wanted, and my roommate put everything on her credit card. It wasn’t long before my roommate and I realized our senior suitemate never offered to pay for our grocery runs. Then she started hoarding certain items for herself. And when we went out to eat on campus, she would always ask one of us to put it on our meal card because she didn’t have a meal plan of her own. Never once did she pay for anything to do with us. We were just a couple of teen girls she mooched off of. Thankfully, at the end of freshman year, my suitemate graduated, and I never spoke to her again.”

What an expert suggests you do:

When it comes to money and shared expense like groceries, rent, or utilities, Degges-White says it’s essential to talk about arrangements early on before any conflict arises. Not only does it establish expectations, but it also helps everyone understand each others’ financial priorities so resentments don’t fester.

“There might be an expectation that people take turns divvying up the grocery buys, but once both freshman friends had taken their turn, they needed to let the senior suitemate know that it was her turn before they piled into the car for the third trip,” she says.

It’s also important to set clear financial boundaries. “If you aren’t willing or able to cover the expenses of another person, then just say no to their request,” she adds. If you don’t have open communication about the issue, people will continue thinking that you’re OK with their behavior and the financial arrangement.

Sam*, 28

“I lived in New York with a roommate during my first year after college. My roommate and I loved to go out together and live the good life, frequenting restaurants, bars, and clubs. Usually I ended up paying the bill and she would Venmo me back for convenience, but after a month or so of living together, the Venmos were getting completed later and later.

“Eventually, it started being several months before they were getting paid. I initially felt too uncomfortable to mention it to her, but I eventually had to bring it up after we went on vacation together. Covering several thousand dollars of expenses for a few months started to feel like an interest-free loan rather than just a delayed Venmo request. Luckily, we were able to resolve the issue after our discussion, and are still friends.”

What an expert suggests you do:

While Sam did the right thing in this situation, Degges-White says she could have avoided the stressful situation by having the conversation earlier. “Talking about intermingling finances is not easy, and most of us expect friends to treat us with the same respect with which we treat them,” she says. “However, when they are slow to repay loans we make to them out of care and friendship, resentment can build and cause a deep rift in the relationship.”

Fortunately, Sam had the conversation early enough that the relationship was able to be salvaged from a situation that might have broken another friendship.

Erin*, 26

“A friend of mine is always saying how tight money is, and I get it. We live in New York City, and she's working so hard to make her dreams a reality. I support her 100%, but it's recently become an issue where I will pay for her things, Venmo request her, and it will go unanswered for months.

“When I ask for an ETA, she explains that she’s already budgeted every dollar for the month and she doesn't have room to pay it off right now — which would be fine if I also didn't see snaps of her at expensive restaurants and going out spontaneously with other friends. It’s a tough balance to be supportive while also creating boundaries to not have my niceness and patience taken advantage of.”

What an expert suggests you do:

In this situation, the person who is bankrolling their friend’s expenses should take a step back and re-examine the situation, according to Degges-White. “Erin’s friend may be choosing to live beyond her means, and that choice is the friend’s alone,” she says. “Not everyone has the funds to live the life that they wish they could afford, and there’s no reason Erin should feel obligated to bankroll her friend’s entertainment or have her Venmo become the ‘Bank of Erin.’”

In addition, Degges-White says there’s a chance that Erin’s friend could also be borrowing money from her other friends just as frequently to live a lifestyle she can’t afford, and she will continue taking advantage of Erin until she puts her foot down. “Based on Erin’s response, the friend might feel that the long delays in repayment are OK and might even be hoping that Erin will eventually lose track or forget about past debts,” she says.

If Erin wants to spend time with the friend, she should let the friend know it’s her turn to pay or choose an activity that is not a major financial investment.

Brittany, 24

“An old friend once bought me a season pass to Six Flags, which I didn’t want and had to repay. I was working a lot at the time and knew I wouldn’t be able to go more than once or twice. Still, she insisted.

“Based on what she told me, I was under the impression that everything was covered on the pass. But when we got there, her pass had the food voucher on it and mine didn't. I barely had any money for food because she had assured me it was all included, so I wound up buying something small. She bought a whole meal, ate part of it, and then threw the rest away. She wouldn't even let me have the rest of it. Unsurprisingly, we weren’t friends for much longer.”

What an expert suggests you do:

According to Franco, incidents where your friends are dishonest about costs at your detriment can shed light on your friendship as a whole and, depending on how things are handled, are a sign that you might need to re-evaluate the relationship. “I think it this case, it would be important to assess whether this behavior is part of a larger dynamic within the relationship because it’s pretty concerning if your friend is asking if they can have some of your food, and you say no,” she says.

However, if this is a friendship you want to salvage, Franco suggests having an open conversation with your friend about how you thought the food was included and ask her why she didn’t share this information with you.