business friends money

The Business of Friends and Money

The holidays are getting close and money seems to be on everyone’s mind.  I have been asked to contribute my thinking on a lot of different subjects this year, and “asking for money” was one of the two that I thought was the most fun (the other was about Lady Gaga and Bradley Cooper).  The reason this subject was so much fun was because of the countless number of times I have been, or have been told about, instances that became very uncomfortable around money, friends, and business.

Just remembering how many times ‘truffles’ have ruffled more than one dinner guest, has made me laugh.  Having lived a long time, I have gone through many iterations about who pays for what.  As a teen, boys paid for everything.  As an adult, whoever did the ‘inviting’ paid.  As an older adult, our social group always split the bill equally.  Regardless of the generalities, during each stage, there were awkward moments.  Seems each generation faces this problem.  I remember my daughter Dana sharing a story about going to a gourmet pizza place with a group of young couples.  Pizzas averaged about $15.  One young woman ordered her pizza with truffles, costing $35!  About the same time, I was out with a mixed group of acquaintances and business associates.  There were about 10 of us.  Three people ordered their steaks with truffles (adding $50 per dish).  When it came time to split the bill there was definitely stress in the air!

This article ran in both InStyle and Yahoo Finance

My Friend Backed Out of Plans and Won’t Pay Me Back for the Tickets

The worst part? She was the one who suggested we go.

By Amanda Richards

Petty Cash
 is a weekly advice column where the experts (plus a millennial InStyle editor well-versed in pettiness) weigh in on your awkward and annoying financial faux pas.


Recently, my friend suggested we go to a women’s conference. I agreed, and since I was the one online at the time, we agreed that I would purchase two tickets — they were non-refundable — and she would pay me later. When the conference rolled around, she got sick and couldn’t go. I felt bad, but that meant I didn’t go, and she also stuck me with two tickets to this thing that are now on my credit card. She knows she owes me money, and she never paid me. How do I bring this up with her in a way that gives me the best chance of getting paid back?

GENERAL UNPLEASANTNESS with regards to money and friends is precisely what inspired this advice column. In the early stages of brainstorming Petty Cash, the InStyle editorial team sat around a table and shared their uncomfortable interpersonal money situations. Some had cheap boyfriends. Others had financially meddling mothers. But everyone — and I mean everyone — had a story about a friend who owed them money, and no one felt particularly good about how the confrontation (or lack thereof) went down.

I shudder at the thought, and I’m not the only one. According to a nationwide study conducted by Bank of America in 2017, 44 percent of people surveyed site money as a key stressor in their friendships, and 50 percent said that they have a hard time bringing up money issues with their friends. In fact, general discomfort with this kind of confrontation and communication means that lots of people end up with forever IOUs — 71 percent of those surveyed said they loaned friends money that hasn’t yet been paid back. The number was so high, in fact, that it inspired Bank of America to institute Pay Back a Friend Day, which happens every year on Oct. 17.

I don’t recommend waiting that long to handle this situation.

The fact that you’re seeking advice on how to start this conversation shows that you clearly have a vested interest in handling this properly. I respect that — not everyone would be so cautious. Additionally, facing uncomfortable situations with someone you care about in a respectful manner (as opposed to ignoring it, or getting too angry), is great practice for the other relationships in your life. In other words: you’re going to have to call people out sometimes, and figuring out how to do it with a friend can be excellent practice.

RELATED: I’m FriendsWithh My Boss and it’s Costing Me Money

Of course, there’s much more to it than just walking up to your friend and asking for money.

“How you phrase your request to discuss the topic is as important as the topic itself,” says Dr. Andrea Goeglein, psychologist and founder of “A potential starting point could be, ‘Jane, I have something that has been troubling me. I want to schedule a time for us to talk about the women’s conference we had to cancel. When can we sit and grab a coffee to talk about it?’”

Even if you’ve been understanding about the fact that your friend was sick (as opposed to simply flaking), the fact that she knows she owes you money might have her defenses up. By setting up a dedicated time to talk it through, you can help avoid the tension that comes with putting someone on the spot, theoretically making her more open to what you have to say — or at least demonstrating that you’re not trying to ambush her or make her feel bad.

When the time arrives to have the conversation, remember that you’re talking to a friend and not just “someone” who owes you money. Stay calm. Though you have a right to be frustrated, try not to let your frustration set the tone for the conversation — instead, approach it as if you earnestly want to get to the bottom of why she hasn’t offered to pay for her ticket yet.

Dr. Goeglein says to start by saying that you were bummed you didn’t get to go to the event together. “[Tell her that] when life had other plans, you were disappointed, and that in addition to the disappointment of not being together, there is also the issue of the financial commitment you had both made.”

RELATED: How to Deal With That One Friend Who Always “Forgets” Her Wallet

Once you start the conversation clearly as friends connecting openly and honestly with one another, Dr. Goeglein says it’s time to make sure you’re both on the same page regarding the choice to attend the conference together, and that your friend understands that she is responsible for holding up her financial end of that choice.

“Once your friend has told you what she understood her commitment to be, it is time for you to agree or disagree,” Dr. Goeglein says.

Of course, that’s where it could get tricky. Maybe, for whatever reason, your friend totally disagrees that she owes you money. She could have assumed that you’d just invite someone else, and that person would pay for the ticket. Perhaps she thought you’d put the tickets up for sale and recoup the cost. Or maybe she made a judgment call and decided that it wouldn’t be a big deal for you to simply pay for the unused tickets. That’s not fair (and not really her call to make), but if that’s the case, you have to be comfortable saying that to her. Ultimately though, you may just have to eat the cost of the conference and reconsider making any financial commitments with her in the future. Additionally, consider the fact that as a friend, she’s demonstrating a lack of understanding and care for your position — and if that’s the case, how good of a friend could she really be?

On the other hand, she might agree that she owes you, but has a specific reason she hasn’t paid you back yet. If she simply doesn’t have the money right now, perhaps you could agree that when the next event rolls around, she’ll be the one to pick up the tickets. If she wants to make good on this commitment, have a conversation about a repayment plan that works for both of you. It might not be your ideal outcome — who wouldn’t be happiest if their friend simply cut them a check right then and there? However, flexibility from both parties might be what it takes to settle the debt between you and preserve your friendship, and ultimately, that’s priceless.


Feel the spirit of the season
About the author

Andrea Goeglein is part organizational psychologist, part entrepreneur, and all about success—your success. She understands both the pressures you face and the dreams that inspire you. Andrea merges her experience as a business owner with her training in Positive Psychology to provide effective, efficient and challenging personal development products and services. She combines an emphasis on objective assessment with an approach that is always powered by your spirit and guided by your goals. Her professional development offerings are based in theory and backed by direct business knowledge.

Related Posts

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.