Pay Dirt

My Friend Always Conveniently “Forgets” to Venmo. So I Devised a Plan.

I am tired of her cheapskate ways.

Woman holding a phone and looking off to the side.
Photo illustration by Slate. Photo by dikushin/iStock/Getty Images Plus.

Pay Dirt is Slate’s money advice column. Have a question? Send it to Lillian, Athena, and Elizabeth here(It’s anonymous!)

Dear Pay Dirt,

“Andrea” is an early 30s woman in my friend group. I’m not her biggest fan, though I keep it cordial. Andrea has a good job and makes about three times my salary. For a friend’s birthday in June, we booked a private karaoke room for a dozen of us. I was in charge of booking and collected the money via Venmo to cover the cost, so I am well aware that neither Andrea nor her then-boyfriend contributed to the cost. The two most well-off people in the group hogged the mic despite not contributing $20 each to our evening though several other people on very tight budgets did.

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Recently, a good friend mentioned that her new partner had enjoyed this particular venue we’re fans of. They have a fun event for small groups that costs $50 a person. It’s hard to find an opening for this, so when I saw that an entire evening was free in a few weeks, my friend and I quickly decided that I would book the reservation and pay the total cost upfront, and everyone would reimburse me. Within a few minutes, we’d sent out a text to those we wanted to invite. Andrea was invited because her roommate and best friend “Toni” is very well-liked and loyal to Andrea, so we knew if we wanted to hang out with her, we would need to invite Andrea. I also didn’t want to exclude her because she happens to annoy me, so I was happy to ask her if she wanted to come along in the spirit of being a mature adult.

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The other six people sent me money for their tickets within a few days. I gave Andrea a week and then sent her my Venmo and reminded her about the reimbursement. She responded, “Oh yeah! Forgot!” When another week passed, I used the Venmo app to request $50 from her, and she never responded.

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This brought us to the week of the event. I texted Toni and let her know I was having trouble reaching Andrea about paying me back for her ticket, and asked her if she could pass along a reminder to Andrea to check her Venmo for my request. She apologized and said she and Andrea were cooking dinner so she’d ask immediately. Three days before the event I still hadn’t been paid, so I invited another friend of mine, who paid me right away. I did not let the rest of the group know about the guest list change.

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The night of the event, Andrea showed up with Toni and I had to tell her that there was no room for her since the reservation was for eight people. She was very embarrassed and so was Toni. I very quickly told the group that I’d tried to reach Andrea several times over the course of the last nearly month, but she never responded, and that I simply could not afford to cover her ticket. Toni and Andrea are very upset, though the rest of the group seemed to think I was reasonable. Could I have done something differently? I am just tired of her cheapskate ways.

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—Rich Friend Is a Cheapskate

Dear Rich Friend,

I get being angry that Andrea is neglecting to pay her share in these situations, but I would have handled the last scenario a little differently. I would’ve made it clear that if Andrea did not pay you, she would not have a ticket. She probably assumed the event worked like the previous karaoke party and that she would be able to pay you later.

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You also suggest that she’s rich and, well, unfortunately, sometimes rich people are oblivious to the extent to which what they consider a nominal amount of money might be an important amount of money to other people. This is not an excuse, just an observation that Andrea may not understand the stress her failure to chip in what she owes is putting on you and others, or that it results in you subsidizing her night out.

That said, you did make reasonable efforts to collect before the event, so Toni and Andrea shouldn’t really be that angry about it. If they are, it may be because you already have some obvious tension, and they may assume that you intentionally left Andrea out. What you should do about it really depends on whether you want to repair those relationships. If you do, I’d suggest the next time you have an event and you’re organizing, you preface your request for their portion of the expenses with an acknowledgment that you did not mean to leave Andrea out last time and want to prevent it from happening again. If Andrea still chooses not to pay her share on time, you made every best effort and Andrea just won’t get to participate.

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Dear Pay Dirt,

I cut off my parents because of their continual financial abuse of me (I was paying “rent” at 14 when I got my first job). It was a long and draining process that took me years to overcome. My problem is I am seeing the same pattern with my younger brother. I always regretted that cutting off my parents meant cutting him off since he was just a kid. We reconnected last year.

My brother is “trying” to save money to go back to school but constantly blows through his paycheck on idiotic crap—like $700 worth of fireworks for July 4th. Then he calls me up to “borrow” money because the rent or car payment is due. He does pay me back, eventually. But every time I try to talk to him about his reckless regard towards money, he shuts the conversation down. It is none of my business right up to when his rent is due. Several months ago, I told him not to ever ask me for money again. He blew up at me and blamed me for his truck getting repossessed. This was right after he and his girlfriend posted a ton of pictures of them going gambling.

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We didn’t speak for several weeks. My brother did extend an olive branch to me and asked me to come down and visit. Only when I visited, my brother and his girlfriend wanted to go out to eat every night at very expensive restaurants. I immediately saw it as a trap so I proposed that I cook for them instead. My brother and his girlfriend ate my food, but the atmosphere was decidedly sour. When I got home, I broke down in tears. I am getting flashbacks to our parents. Is there any point to keep trying? Or should I just bite the bullet and cut my brother out of my life again?

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—Older Sister

Dear Older Sister,

You have more options than cut your brother out of your life or keep loaning him money. Whether you can really help him break the unfortunate pattern your parents established is a matter of why he’s struggling in the first place. If it’s a matter of not knowing how to manage money, then it may help to set him up with a few budgeting resources. We’ve covered the basics of budgeting extensively in this common—that can be a place to start.

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Now, if it’s a matter of just assuming you will backstop him whenever he needs money, that’s a different story. In that case, you don’t need to cut off communication with him but you need to let him know that you can’t keep helping him financially. He has a job and needs to learn to support himself—that means not blowing money on gambling, and cooking at home instead of going out to eat every night.

Tell him that you want a relationship with him, but it cannot be contingent upon you loaning him money. You are not a bank, and you don’t owe him this kind of help. You should also explicitly explain to him that it was very painful for you when your parents did similar stunts like this and it’s not OK for him to put you in a similar position. If he values your relationship, he should understand. If he doesn’t, then I think you have to accept the possibility that his only interest in having a relationship is using you as a financial safety net.

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Dear Pay Dirt,

My girlfriend makes at least three times more than I do (I don’t know exactly how much, but she didn’t qualify for a COVID stimulus, so I know it’s a lot), and she’s always complaining that she’s barely making ends meet. But she’s got money to pay someone to clean her house and go to NYC three times in the past year, plus LA at least once. Meanwhile, I’m actually struggling (canceling all my subscriptions and streaming services, haven’t eaten out in over a year, have zero “fun money” per month, etc. ) and it drives me nuts when she complains because I don’t think she has any reason to. Some of us are actually barely making it. It baffles me how someone could earn so much, and still struggle every month. Should I just let it go? It’s her money, after all. But I can’t stand her complaining about it all the time when it’s her own doing.

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—Pinching Pennies

Dear Pinching Pennies,

I understand why this is frustrating, but unless you’re subsidizing her expenses, I would err on the side of not evaluating them. If you had shared assets and responsibilities, this would be a shared problem. But that’s not the case.

Still, you two should talk about the tension this is creating. It sounds like she doesn’t really understand the gravity of your situation or she’d be more sensitive to the issue. You should let her know that you’re struggling and explain in detail that you can’t afford the sorts of experiences she’s spending money on. While you respect her right to spend her money however she pleases—because it’s her money—explain that it’s straining your relationship to hear her complain about not being able to make ends meet when she can afford so many trips and luxuries that you can’t.

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If she agrees that the problem is partly because of her spending, then you may be able to encourage her to think about money in a different way. She can examine where she can cut non-essential expenses. You could even help her make a budget. If she dismisses the idea and continues to complain, I think you have to set a hard boundary and tell her it’s a topic you don’t want to discuss if she’s not willing to address the cause of her overspending. If she keeps doing it anyway, change the subject or end the conversation.

Dear Pay Dirt,

I was let go from my job this week due to company-wide layoffs. Fortunately, I got a severance package and have emergency savings. If I cut back on flexible spending, I have enough money for about a year without needing to generate income. While I don’t plan on taking an entire year off, I would like to take four to six months.

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I am newly married with no kids so my finances are not combined with my husband’s. We only share living expenses. We have been splitting these expenses based on income, so I was paying 75 percent and he was paying 25 percent. He makes a decent salary and could cover the majority of our shared expenses himself.

I want to renegotiate how much each of us is paying while I am not working. If I pay less, I would have the money while I have the time to travel more, and more cushion when I do decide to look for work again to find something I really want. On the other hand, I could continue to pay as much as I have been and still be OK for a year. What is the fair thing to do in this situation? How should we think about how to split our shared living expenses while I am not actively looking for work?

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—What’s Fair

Dear What’s Fair,

It depends on whether you focus on what’s fair in terms of responsibilities or what’s fair in terms of outcomes. If you’ve been splitting expenses a certain way because you had a more signifcant income, and suddenly you don’t, yes, it’s reasonable to want to re-negotiate your expenses. That said, the effect of doing that will be that your husband will pick up more of the expenses and he may not be prepared to do that financially or in other ways. You need to consider that. It may create some resentment, especially since you’ll be taking a big chunk of time off to do activities like traveling and think about what you want to do next. You are absolutely entitled to those things, and to spend your money however you want, but there’s no getting around the fact that if you renegotiate, you are shifting some of the burdens to your husband.

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Ultimately, this a matter of starting a conversation with your husband that frames the issue in terms of equity. You’ve been covering most of the expenses so far, and I’m sure he would find it reasonable to expect a different ratio if his income were much higher than yours, and now it is. But also note that you realize this would mean he’d take on more of the expenses while you’re taking time off and ask what he thinks is fair first. Have him suggest a percentage. There’s no “right” solution here, only what feels fair and reasonable to both of you. The conversation will go more smoothly if you have him make an “offer” for what he thinks is reasonable. It may be a number you’d happily accept, and then your problem is solved. If not, at least it sets a baseline for what he thinks his obligations are, and you can make an argument for an increase. The conversation you want to have is not you telling him you want to pay less of the expenses, but something more along the lines of “How can we make this more equitable for both of us?” You mention that you’re newly married, so now is a good time to develop a habit of framing dilemmas like this as something you solve together.

—Elizabeth

More Advice From Slate

My sister and I are in our mid-30s and we don’t get along. When holidays and birthdays roll around, I text her to ask for her kids’ wish lists so I can buy them presents. She usually replies by phone, with some version of “The only thing my kids want is their mother to be happy, and our relationship makes me very sad.” And I’m like, “OK, but my gifts to your kids have nothing to do with our relationship.”

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