Money + Love Part IV: Navigating Finances With Friends

About the Episode

Discussing finances with friends? Talk about awkward… Unless, of course, you use the great tips from this episode of Making it Count! Our hosts Cristina and Will were joined by returning guest Richard Barbari from Addition Financial and new guest Erin Papworth, the Founder and CEO of They covered a whole spectrum of money topics as they relate to friendships – like how to navigate the dreaded bill splitting conversation at the end of dinner or what to do if a friend asks to borrow money.

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Will asks Question 1: “Erin, do you think it is a good idea to talk to your friends about money – and if so, why?”

Erin responds: “It depends on the relationship you have with your friends. Money is a personal and complicated topic. There are negative societal triggers about money such as shame, embarrassment and guilt. I think our society has made the mistake of attaching self-worth to our wealth, which is so the opposite of true.”

“However, talking to your friends about money can demystify the taboo around it and help you see how other people manage their finances. I come from a behavioral science background and one of the key verticals that we use to try and help people change behavior is peer-to-peer education. Basically, people from your same walk of life, with your same issues talking about the subject. It really helps you brainstorm together, think about things differently and see how other people think about the questions you're asking in life.”

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“I think this is a really powerful piece to how we learn as humans. If you look at other topics in life you probably learned a lot over the course of your education from talking to your friends – as much as the actual educators. So yeah, there are a lot of benefits to it, but you should take it case-by-case based on who you trust. I also wanted to mention that you are 20 times more likely to save when you discuss money with others.”

Cristina asks a follow-up question: “So is it similar to when people start diets or exercise with friends, they hold each other accountable?”

Erin responds: “Yes, very much! You normalize it by taking the discussion out of your own bubble or headspace. You share what you’re struggling with, the solutions you’ve found and ask others what they’ve done. Basically, problem solving with others – that’s how we learn in life.”


Cristina asks Question 2: “Is there a right way to talk to your friends about money?”

Rich responds: “I think conversations about money will come organically if both parties are comfortable with it. An example with me personally, I had a friend who had a financial question for me and I gave him a real, fair answer that didn't go into too much information. He was comfortable sharing some of his financial information, but I didn't ask for any more details about it. Then slowly after that it grew into something that every once and a while we talk about our situations.”

“I think Erin made a really good point about people correlating what they earn with their worth. We all have friends that think that way and it can be pretty easy to spot who those people are. I would say you might want to avoid having financial conversations with them, especially if you don't make as much or save as well as they do. Remember, you're sharing information when you have these types of conversations that could be shared with other people or made into a joke – and that can hurt you even more financially in the long run.”

Will responds: “To your point Rich, I think that’s a moment in life when you need to evaluate who you are getting close to. You don’t want to be in a position where someone is constantly putting you down or you’re comparing yourself to others in a competitive way.”


Will asks Question 3: “Now, I want to pivot to something that’s probably the only way some of our listeners talk to their friends about money, and that’s splitting expenses when you’re all out together. Erin, what’s the best way to navigate those situations?”

Erin responds: “We’ve all been there before; splitting dinner with your friends can feel incredibly painful and awkward. As you approach that situation, it’s always good to put yourself in someone else’s shoes. Try to anticipate if one or more of your friends are not comfortable with splitting the bill a certain way. It’s really a case-by-case scenario based on your friends’ openness to having those discussions beforehand.”

“And then if you’re the one that isn’t comfortable evenly splitting the bill, then it’s up to you to communicate that beforehand. Focus on an open and transparent conversation because really money is just money. It’s a social construct or form of exchange. We put all this weight and worth to it and it’s time for society to break away from that thought. We’re all on different paths, have our own journeys, our personal purpose in life, our passions and the things we want to spend our money on, the things we place value in, and the work we do. And by just talking about finances, we break those negative connotations.”

“Honestly, just saying, ‘Hey, I don’t have the money for this.’ Or, ‘I’m going to split the bill because I only got a salad and you all drank too much.’”

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Cristina asks Question 4: “Rich, what do you recommend if someone doesn’t want to pay their fair share?”

Rich responds: “I’ve definitely had this conversation with my friends one too many times. Like Erin said, this situation comes up for most people when they go out to dinner. I’ve learned to have this conversation with my friends before we go out to dinner. Saying, ‘Hey, what do we want to do about paying the bill?’ This is especially important if you don’t plan on drinking, but your friends are going for that reason.”

“Having that conversation at the beginning of the night is worth it for me because, as the night progresses, you don’t want to be drowned out by the three or four friends that end up wanting to just split the bill evenly when you only had a $10 meal and they had a variety of food and drinks.”


Will asks Question 5: “Talking about a bill is one thing, but, Erin, how can people break the ice with their friends and get the ball rolling for a bigger conversation about money?”

Erin responds: “I think we are all speaking to this point of transparency. One of the things we see is that asking for advice on a topic, but not making it too specific, is always a good place to start. Asking a friend how they went through the process of buying a house or if they have student loans. Really just leaning into a normal conversation, like an advisory approach, often breaks the ice. Everyone is navigating the financial system by virtue of us all being adults, so there are those broad topics you can start with and then dig into those deeper pain points.”

“What’s interesting right now is this whole new world of online finfluencers (financial influencers) that all tend to have their specialities – like, paying off $100,000 of debt before 29 or flipping your house or managing your 401k. You can find a finfluencer on a topic that feels pressing to you and dig in there to get advice that’s not too personal.”

“There is a lack of financial confidence in our country because we have such low education on finances, which I think is a systemic problem. This creates a gap in the market for these finfluencers to come in and have a place in the dialogue. I hope we can start to invert that conversation and get a population, especially the generation growing up now, that isn’t as reliant or impacted by these finfluencers. It seems like Gen Z and the late Millennials (Zillennials) are more confident about money.”


Cristina asks Question 6: “Rich, what’s the best way to handle splitting expenses with roommates?”

Rich responds: “I think splitting expenses with roommates is very similar to splitting a check at a restaurant. You need to talk about finances before you move in or even sign on the dotted line on renting a location with a new roommate. The first thing you need to figure out is rent. Make sure that price is something all of your roommates can comfortably afford. Because if it’s super close to someone’s budget, there’s a chance they might miss a month of rent in the future.”

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“Next, you should create an in-house budget with your roommates. Talk about splitting up the utilities and rent, because most of those expenses are in one person’s name. Have a budget set up in place and decide who’s paying for what, how you’re going to transfer the money and when the due dates are. Take a day to discuss all of these expenses before moving in with each other.”

“This way there are no sticky situations or uncomfortable conversations between the two of you. It’s really not difficult to do, it’s just that most people don’t do it, especially with friends that move in together. It’s not uncommon for there to be rifts in friendships because of the financial side of moving in together. You’ll sometimes have that one friend that’s always on top of their finances and the other that’s not, which can lead to a tough situation.”

Cristina responds: “I’m sure lots of friendships have been ruined because of this situation. If I’m the one taking responsibility and my roommate doesn’t pay their half, that’s my credit that’s being hit. It’s a big gamble to have a roommate and not put that structure out there from the start.”

Will responds: “There’s also working out if you’re evenly splitting the rent or not based on who has the most ‘personal space.’ I had one living situation where I was getting the larger space and the ensuite bathroom, so I paid more of the rent because I did not want there to be any issues down the road. When you’re first signing the lease, everyone is excited and fine with the decision, but a few months in, people might start questioning it. So set yourself up for success to not have to worry about those conversations ever coming up.”


Will asks Question 7: “Now I want to get into a really sticky topic. Erin, should you ever loan money to a friend?”

Erin responds: “Borrowing money from friends and family is definitely tricky, but that doesn’t mean it has to be bad. Typically, it’s a case-by-case scenario that depends on your comfort with loaning money in general. The key is determining the ground rules and loan terms in the beginning. Being transparent and writing down the agreement can help ensure you’ll get your money back without ruining the relationship.”

“I think there’s a tendency in our world to be casual about finances with our friends because it is such a touchy subject and people have different levels of interest and perspectives on it. But if you’re truly wanting to get your money back – and maybe you even want to charge interest on it since it is an investment – then you really have to make sure you set the terms and stick with the agreement.”

“You should understand the risk of souring the relationship and the risk of possibly never seeing the money again because trying to litigate a personal loan that you made to a friend just sounds like a complicated road to go down. So making sure everyone sticks to the loan agreements from the beginning is key. It is very dicey though.”


Cristina asks Question 8: “Rich, what about saving and retirement topics? How should people talk to their friends about those things?”

Rich responds: “I think your age makes a big difference. If I was in my early twenties starting out with a new career, then I’d want some advice on 401ks or other retirement packages. I’d also feel more comfortable talking to my friends about this topic since I’m only asking them for the best practices. If you have any friends that work in the investment industry, then it might be a good idea to ask them for tips and advice.”

“As you get older, your friends might give you other tips on what you should do outside of a 401k, like investing in a mutual fund or an index fund. When it comes to saving money, a lot of people get excited about budgeting because it's so simple to do, especially with online tools and apps, like Mint. For example, my friends will often talk to me about their Mint app or a change they've implemented that’s helped them budget easier.”

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Will asks Question 9: “Speaking of growing money, Erin, what’s a good way to ask for or share investment advice?”

Erin responds: “It’s always good to start with a specific question. Start by asking about a 401k or a Roth IRA or ask them when they want to retire. It’s all about starting with a single subject and then moving into specific investment advice. However, it’s important to take everything with a grain of salt. While talking about finances with friends makes you more likely to save, you should be wary about the quality of their advice.”

“We just saw this with the Robinhood meltdown and meme stocks in early 2021 – that was peer-to-peer education and conversations about this one stock. It probably wasn’t in everyone’s best interest or financial future and it made our market go crazy. So use your peers as a sounding board but don’t act on the advice until you do the proper research or talk with a financial advisor.”

“The unique thing about finances is that we are all navigating our own financial health and experiences, so we really need to take ownership of that and be empowered to listen to others and adjust it for ourselves.”

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Cristina asks Quick Question 1: “Rich, my question is for you. What’s the best way to handle the financial aspect of gift giving with friends?”

Rich responds: “That's a very good question. I think you need to set a price when it comes to gift giving because you can find yourself in debt. For instance, if you set a limit for $20 every year, then you don’t have to worry about someone spending too much money on you or returning the favor.”


Will asks Quick Question 2: “Erin, my question is for you. Should you share your salary with your friends?”

Erin responds: “It depends. Only if you feel comfortable and if you think it's going to benefit you or them. We're in an age where transparency and equal pay has been a big conversation in society. Talking about salary with your friends can ensure they’re being fairly compensated for their work.”


Cristina asks Quick Question 3: “What’s a money lesson that you’ve learned from a friend?”

Rich responds: “Points and rewards from credit cards. My friend taught me how to get cool perks, gifts and rewards with my credit card, so without a doubt, it’s my favorite money lesson.”


Rich Barbari is the Relationship Manager in the Community Engagement & Partnerships department at Addition Financial. You can get in touch with him at or call Addition Financial at 407-896-9411 and ask for Rich Barbari. 

Erin Papworth is the Founder and CEO at To connect with her, you can follow their Instagram, Facebook, Pinterest, or Twitter accounts. Erin can be reached directly on her personal Instagram and LinkedIn accounts as well.


In this episode Cristina and Will shared the The Millennial Playbook to Paying off Debt & Saving for the Future. It has tips for paying off student loans, saving to buy a house, starting a family and more.

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