Splitting the Bill With Friends? Navigate Venmo Requests, Unpaid Loans and Money Regrets

Learn how to plan and pay for a sabbatical, plus why cash advance apps may cost more than you think. How do you plan and pay for a sabbatical, even if your employer doesn't offer a paid one? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola are joined by Smart Money producer Tess Vigeland to answer a listener's question about setting up for extended time off work. They talk about how rare paid sabbaticals are, which companies offer them, and how to set goals for your time away. Tess shares the story of her three-year sabbatical in Asia, and the hosts compare the pros and cons of shorter breaks. They also get into building a sabbatical budget and sinking fund, why debt and emergency savings matter even more when your paycheck pauses, what happens to your health insurance, and what it can feel like to return to work. Plus, ways to get a real break when a sabbatical isn't in reach. Why might cash advance apps cost more than their marketing would lead you to believe? Senior news writer Anna Helhoski talks with Candice Wang, senior researcher at the Center for Responsible Lending, about new research on payday advance apps. They discuss how these apps differ from traditional payday lenders (and how they don’t), why users may not recognize them as high-cost loans, how an average 232% APR and frequent repeat borrowing can add up, why some state payday lending laws don't apply, and what you could consider before using one. Explore the Center for Responsible Lending's research on payday loan apps, plus NerdWallet's guides to sinking funds and COBRA coverage: The Cost of Payday Loan Apps in Your State: https://www.responsiblelending.org/research-publication/cost-payday-loan-apps-your-state Sinking Funds: The Secret to Stress-Free Expenses: https://www.nerdwallet.com/finance/learn/nerdwallet-sinking-fund-savings COBRA Health Insurance Eligibility and Alternatives: https://www.nerdwallet.com/insurance/health/learn/cobra-health-insurance Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend! *The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality. Learn more about your ad choices. Visit megaphone.fm/adchoices

Learn how to handle money tension with friends and partners, from splitting costs to getting a loan paid back. Is it fair for a friend to split every grocery bill with you when they earn far more than you do? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola dig into some of Reddit’s messiest money conversations, with posts read by NerdWallet senior banking writer Spencer Tierney, credit expert Amanda Barroso and content strategist Jackie Tucker. You’ll hear why surprise payment app requests can sting, how rarely money values come up between friends, whether splitting every cost makes a friendship feel transactional, and what to consider when a friend borrows money twice and then asks whether they really need to pay it all back. Then, how much money does it take to stop worrying about money? Sean and Elizabeth discuss why there may never be a magic number, how medical bills and rising health care costs feed financial anxiety, and what a viral article about Gen Z women paying for, and parenting, their boyfriends reveals about the difference between a wage gap and an effort gap in relationships. They also open up about the financial decisions they regret (or refuse to), from overstaying in a low-wage job market abroad to not setting money aside for taxes, and react to Redditors’ biggest regrets, including selling Microsoft stock in 1992 and skipping a prenup. Read The Cut article discussed in this episode here: https://www.thecut.com/article/young-women-earning-more-money-boyfriends.html Follow the Reddit conversations discussed in this episode below: Finance Stuff With A Friend At what income or net worth did you stop worrying about money? How To Ask Somebody To Pay You Back What is a financial decision you will regret for the rest of your life? Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend. Learn more about your ad choices. Visit megaphone.fm/adchoices

Learn how to rebuild credit while saving in sinking funds, and why 7 in 10 Americans struggle to afford the basics. How can you rebuild your credit and save for big goals at the same time? Hosts Sean Pyles, CFP, and Elizabeth Ayoola are joined by NerdWallet senior credit expert Amanda Barroso to answer a listener's question about moving from repairing bad credit to building excellent credit. They discuss which habits have the biggest effect on your score and how to spot errors on your credit report. They also cover when a secured credit card could make sense, how rent reporting and credit limit increases might help, and what credit score you typically need for a travel rewards card. Finally, they talk about how to set up sinking funds so the pursuit of credit card rewards doesn't turn into overspending. Then, why are so many middle-class families struggling to afford the basics? Senior news writer Anna Helhoski talks with Lelaine Bigelow, executive director of the Georgetown Center on Poverty and Inequality, about their new Family Economic Well-Being Index. The index finds that 70% of Americans struggle to afford at least one basic need. They discuss why renters face heavier housing burdens than homeowners and why child care strains families even at higher incomes. They also get into why health care is the most widespread burden and how stacked costs can leave a family one surprise bill away from a crisis. Learn the strategies that can help you build your credit score faster: https://www.nerdwallet.com/finance/learn/raise-credit-score-fast Find out how a secured card could help you rebuild credit: https://www.nerdwallet.com/credit-cards/learn/build-credit-with-secured-credit-card See how rent-reporting services could help renters get credit for on-time payments: https://www.nerdwallet.com/finance/learn/rent-reporting-services Learn how sinking funds can help you pay cash for big expenses: https://www.nerdwallet.com/finance/learn/nerdwallet-sinking-fund-savings Check your credit reports for free every week: https://www.annualcreditreport.com Explore the Family Economic Well-Being Index findings from the Georgetown Center on Poverty and Inequality: https://www.georgetownpoverty.org/issues/new-family-index/ Please help us improve the show by taking our listener survey! Your responses directly impact what you hear on the show: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform Subscribe to our podcast’s free email newsletter for bonus content and more from our hosts at https://smartmoney-nerdwallet.beehiiv.com/  Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header Smart Money’s YouTube Channel: https://youtube.com/@nerdwalletsmartmoney To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend. *The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality. Learn more about your ad choices. Visit megaphone.fm/adchoices

Learn how to build generational wealth and navigate the complex financial issues of being the first in your family to get ahead financially. Generational wealth expert India Elliott, a financial advisor at Wells Fargo Advisors, joins hosts Sean Pyles, CFP®, and Elizabeth Ayoola to answer listener questions about building — and protecting — wealth that lasts. One listener, a first-gen college grad who relocated out of a small Ohio town, wants to understand how to build “real wealth” for himself and his family; India walks through her four pillars (earn, manage, protect, and grow) and explains how tools like trusts, life insurance, and estate plans could pass assets to the next generation with fewer taxes and fewer family disputes. A second listener has her own finances in order but struggles with watching loved ones make financial choices that worry her, navigating the concept of the “Black tax,” and figuring out when — and how — to say no to financial requests without guilt or compromising her own path to generational wealth. Please help us improve the show by taking our listener survey! Your responses directly impact what you hear on the show: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend. *The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality. Learn more about your ad choices. Visit megaphone.fm/adchoices

Learn how to turn your retirement savings into a steady retirement paycheck and how grocery stores may use your data to set prices. How do you turn decades of retirement savings into income you can count on for the rest of your life? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola talk with Jean Chatzky, host of the HerMoney podcast and author of “The Forever Paycheck: The New Retirement Strategy to Spend More, Worry Less, and Never Run Out of Money,” about why spending down your savings in retirement can be so hard, both in the math and in your head. They discuss where the 4% rule could fall short, the difference between buying a paycheck with an annuity and building one with investments, and when to start planning. They also answer listener questions about whether a pension means you can ease off on 403(b) contributions, what two years out of the workforce could cost a stay-at-home parent, and whether to consolidate old retirement accounts. Then, is your grocery store charging you more than the shopper next to you for the same items? Senior news writer Anna Helhoski talks with fellow Nerd Amanda Barroso about surveillance pricing, where retailers use data from loyalty programs, apps and even how fast you type to set prices based on what they think you’re willing to pay. They discuss how it differs from dynamic pricing, the signs it could be happening to you, what states and the FTC are doing about it, and how adding a little friction to your shopping could help. Please help us improve the show by taking our listener survey! Your responses directly impact what you hear on the show: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform For more information on the topics discussed in this episode, check out these resources: Retirement Calculator: https://www.nerdwallet.com/investing/calculators/retirement-calculator HerMoney with Jean Chatzky:  https://www.youtube.com/hermoney The Forever Paycheck by Jean Chatzky: https://www.penguinrandomhouse.com/books/805286/the-forever-paycheck-by-jean-chatzky/ my Social Security: https://www.ssa.gov/myaccount/ Why the Box of Cereal in My Cart Might Cost Less Than Yours: https://www.nerdwallet.com/finance/news/surveillance-pricing Federal Trade Commission’s Proposed Enforcement Policy Statement Regarding Personalized Pricing: https://www.ftc.gov/system/files/ftc_gov/pdf/p034101-ftc-enforcement-policy-statement-re-personalized-pricing-proposed-for-public-comment.pdf Subscribe to our podcast’s free email newsletter for bonus content and more from our hosts at https://smartmoney-nerdwallet.beehiiv.com/ Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header Smart Money’s YouTube Channel: https://youtube.com/@nerdwalletsmartmoney To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend. The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality. Learn more about your ad choices. Visit megaphone.fm/adchoices

Learn how condo and HOA fees change the math on renting vs. home ownership, and how to resist a pricey tech upgrade. Is buying a home with a hefty condo or HOA fee worth the money compared with renting? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola talk with Ryan Sterling, CEO of NerdWallet Wealth Partners, about a listener trying to factor condo fees into the rent vs. buy decision. You’ll hear why the idea that renting is “throwing money away” overlooks the costs homeowners might not get back, how long it could take for buying to break even at different mortgage rates, and why the payoff of owning a home can be as much about emotions as finances. Then, how do you talk yourself out of a big purchase you don’t really need? Sean and Elizabeth weigh the pull of Apple’s new $2,000 folding phone and a high-end smartwatch, why monthly installment plans and phone leasing can make pricey tech feel cheaper than it is, and how to tell whether a splurge lines up with your values. Your financial decisions deserve a real partner. Learn more about NerdWallet Wealth Partners here:  https://nerdwalletwealthpartners.com/ Thinking of buying a property? Know the real cost first with NerdWallet’s Rent vs. Buy Calculator here: https://www.nerdwallet.com/mortgages/calculators/rent-vs-buy-calculator Enter for a chance to win a $250 Amazon gift card — and help us improve our show — by taking our listener survey! Find the survey and official sweepstakes rules here: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform?usp=sharing&ouid=102666646608198254961  Subscribe to our podcast’s free email newsletter for bonus content and more from our hosts at https://smartmoney-nerdwallet.beehiiv.com/  Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header Smart Money’s YouTube Channel: https://youtube.com/@nerdwalletsmartmoney To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend. *The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality. Learn more about your ad choices. Visit megaphone.fm/adchoices

Learn how to escape a timeshare contract, plus what kind of help exists if you want to buy a home. How do you get out of a timeshare you no longer want? Elizabeth Ayoola talks with travel Nerd Craig Joseph about a listener whose parents are paying yearly fees on an Orlando property they can barely use anymore. You'll hear why these timeshare contracts are so hard to unwind, what maintenance fees tend to run, and why there's often no cap on how fast they climb. Then, can you really get free money to buy a house? Sean Pyles, CFP®, Elizabeth Ayoola and senior news writer Anna Helhoski are joined by mortgage Nerds Abby Badach Doyle and Kate Wood to discuss how down payment and closing cost assistance works, and how to tell a good deal from an expensive one. They get into where the thousands of programs come from, how a grant differs from a forgivable loan or a second mortgage, and one place homebuying help is starting to appear that you might not expect. Want to get rid of your timeshare? Read this before you hire someone to help: https://consumer.ftc.gov/consumer-alerts/2022/11/want-get-rid-your-timeshare-read-you-hire-someone-help Links mentioned in this episode: How Timeshare Presentations Earn Me Cheap Travel: https://www.nerdwallet.com/travel/learn/how-timeshare-presentations-earn-me-cheap-travel Are Timeshares Worth It? Possibly, if You Buy Smart: https://www.nerdwallet.com/travel/learn/are-timeshares-worth-it Want to get rid of your timeshare? Read this before you hire someone to help: https://consumer.ftc.gov/consumer-alerts/2022/11/want-get-rid-your-timeshare-read-you-hire-someone-help Enter for a chance to win a $250 Amazon gift card — and help us improve our show — by taking our listener survey! Find the survey and official sweepstakes rules here: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform?usp=sharing&ouid=102666646608198254961  Subscribe to our podcast’s free email newsletter for bonus content and more from our hosts at https://smartmoney-nerdwallet.beehiiv.com/  Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header Smart Money’s YouTube Channel: https://youtube.com/@nerdwalletsmartmoney To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend. *The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality. Learn more about your ad choices. Visit megaphone.fm/adchoices

Learn what to weigh before investing in real estate syndications, including costs, risks and REIT alternatives. Should you diversify into real estate, and is real estate syndication the right way to do it? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola talk with NerdWallet investing writer Sam Taube about what real estate syndication actually involves, the different ways to get in — from online crowdfunding platforms to launching your own deal — and the questions worth asking a sponsor before committing any money. They cover how much capital it typically takes, how long that money could be tied up, and why accredited-investor rules can lock out everyday investors. Sean and Elizabeth also weigh the potential tax benefits against the risks, including past scandals at some online platforms, and talk through simpler alternatives like real estate investment trust (REIT) ETFs for anyone who decides a private syndication is more risk and paperwork than it's worth. They wrap up with a candid conversation about financial anxiety on social media and why it's still worth saving even when money feels tight. Check out NerdWallet's roundup of real estate crowdfunding platforms: https://www.nerdwallet.com/investing/best/real-estate-crowdfunding-platforms Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend. *The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality. Learn more about your ad choices. Visit megaphone.fm/adchoices

When a parent sends their retirement savings to someone they met online, learn how to help them recover – without letting it happen again. What do you do when a parent has spent most of their retirement savings on a romantic partner they’ve never met? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola help from a listener whose father, in his 70s, drained his retirement accounts and ran up massive credit card debt paying someone he met on OnlyFans. Sean shares what happened when his own father lost $150,000 to a crypto scheme while isolated during the pandemic, and Elizabeth talks about being scammed herself and her mother handing money to a stranger promising crypto returns. They get into the shame that keeps victims silent, the chat agencies that mean the person answering may not be the person in the photos, the red flags that show up before money moves, and why a parent who’s lonely is a target long before they’re a victim. Plus, we talk with an economics professor about the Federal Reserve’s decision this week to hike a key interest rate, and what it could mean for your loans and savings accounts.  If you’re worried a parent is being scammed, you can access free guidance at the AARP Fraud Watch Network Helpline.  Enter for a chance to win a $250 Amazon gift card — and help us improve our show — by taking our listener survey! Find the survey and official sweepstakes rules here: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform?usp=sharing&ouid=102666646608198254961  Subscribe to our podcast’s free email newsletter for bonus content and more from our hosts at https://smartmoney-nerdwallet.beehiiv.com/  Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header Smart Money’s YouTube Channel: https://youtube.com/@nerdwalletsmartmoney To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend. *The show notes were created with the assistance of AI. They have been reviewed by our editorial team for accuracy and quality. Learn more about your ad choices. Visit megaphone.fm/adchoices

Is indexed universal life insurance “recession-proof?” Learn how it really works and whether it belongs in your retirement plan. Hosts Sean Pyles, CFP®, and Elizabeth Ayoola speak with NerdWallet insurance writer Elizabeth Aldrich about what IUL actually is. Aldrich breaks down the zero-percent floor that sounds like guaranteed protection (but doesn't mean you can't lose money), the truth behind the "better than a 401(k)" and "tax-free retirement" claims circulating online, and the narrow circumstances where an IUL might actually make sense.  Read Lizzie's NerdWallet article on why “recession-proof” insurance is trending: https://www.nerdwallet.com/insurance/life/news/indexed-universal-life-insurance-trending  Enter for a chance to win a $250 Amazon gift card — and help us improve our show — by taking our listener survey! Find the survey and official sweepstakes rules here: https://docs.google.com/forms/d/e/1FAIpQLSettbeI0yDf8tLt_Q772StVJoWs_Gm-pWa-gSn2fdWEc0XcOw/viewform?usp=sharing&ouid=102666646608198254961  Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header  To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [email protected]. Like what you hear? Please leave us a review and tell a friend. Learn more about your ad choices. Visit megaphone.fm/adchoices