It’s bound to happen in any friendship: an unfulfilled Venmo request, a trip that’s way out of your budget, or a dispute over splitting the bill at a restaurant. This week, we’re answering your questions about navigating tricky money situations with friends.

Reema is joined by comedians and real-life friends Josh Gondelman and Alison Leiby to talk through everything from expensive bachelorettes to Venmo nickel-and-diming.

If you liked this episode, share it with a friend. And let us know what you think by emailing uncomfortable@marketplace.org or calling 347-RING-TIU.

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For a lot of us, money is a source of anxiety and guilt. Reema recently joined the podcast “Happier with Gretchen Rubin” for a roundtable conversation with Gretchen and Haley Sacks (a.k.a. Mrs. Dow Jones) about why money feels so emotionally loaded – and the small, realistic changes that can make managing it feel easier.

Maybe you’ve heard that little voice: What if I could make a little money from this? The urge to monetize your hobby can feel tempting, but is it worth it?

Reema talks with people who’ve tried to turn their pastimes into side hustles and finds out what they’ve gained, lost and learned along the way. Then, she speaks with a leading expert on creativity about how money can quietly reshape our motivation – and how to keep our hobbies from turning into just another job.

If you liked this episode, share it with a friend. And let us know what you think by emailing uncomfortable@marketplace.org or calling 347-RING-TIU.

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Steve Burns didn’t set out to become a children’s TV icon. He moved to New York with only a duffle bag full of clothes, $300 in his pocket, and a dream to become an actor. When Steve got hired to host “Blue’s Clues” from 1996 to 2002, he found himself disoriented by fame and uncertain of his career trajectory. Reema talks with Steve about finding meaning outside of work, feeling like an imposter in a role he never expected, and how he redefined his money values … when he escaped to the forest.

Have you ever struggled with imposter syndrome in a new job? We want to hear about it, so give us a call at 347-RING-TIU or send us an email at uncomfortable@marketplace.org.

And you can check out Reema’s interview on Steve’s podcast, “Alive with Steve Burns” here.

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With more layoffs in the news, a lot of workers are feeling spooked. It can be hard not to spiral into what ifs: What if the next paycheck is my last? What if I can’t find another job?

We look at how to cope with that uncertainty and what you can do to help protect yourself. Reema talks with psychologist Ellen Hendriksen, career coach Melody Wilding, and financial educator Jannese Torres, who share practical ways to stay grounded and prepared – from reframing your anxiety to strengthening your safety net.

Have you ever struggled with layoff anxiety? We want to hear about it, so give us a call at 347-RING-TIU or send us an email at uncomfortable@marketplace.org

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Think that a prenup isn’t for you? Think again! Prenups are not just for rich people: they can protect you against debt and mitigate future issues like spousal support and custody. You’ve got to talk honestly about money if you want to build a shared financial life together, while still protecting yourself. This week, Reema Khrais talks with family lawyer Sahar Taylor and financial therapist Aja Evans to understand how prenups work and the deeper emotions underneath.

If you liked this episode, share it with a friend. If you have thoughts, strong opinions about prenups - if you’ve signed one or are trying to decide if you should - we’d love to hear about it! You can email us at uncomfortable@marketplace.org or call 347-RING-TIU to leave a message.

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Correction (Feb. 20, 2026): Previous versions of this story misstated the percentage of prenups among married Americans.”

Reema is joined by Sam Sanders (host of KCRW’s “The Sam Sanders Show”) to answer your questions about money and dating. We’ve got questions about scammers, secret investments, and secondary partners.

If you liked this episode, share it with a friend. And if you have a sticky money situation you need advice on, call and leave us a message at 347-RING-TIU or email uncomfortable@marketplace.org

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How much do you share with your partner about your finances? Sometimes, a little privacy starts to look a lot like a secret. And secrets (especially the money kind) have a way of becoming problems.

On this week’s episode, Reema talks to people on the streets of Portland about their real-life money secrets, and chats with divorce lawyer Randy Kessler and couples counselor Jeff Guenther, who’ve seen how financial secrecy can fracture relationships — and sometimes bring people closer.

If you liked this episode, share it with a friend. And let us know what you think by emailing uncomfortable@marketplace.org or calling 347-RING-TIU. Have you ever kept a big money secret from your partner? We want to know! And follow us on Instagram and Tiktok!