The Real Question

Is the way I'm spending my time aligned with my values?

16 Mar 2026

Contributed by Lukas

Emily is a new mother finally finding the balance between time for her daughter and time just for herself. She's a reliable and consistent friend, a ...

A Prompt from Mauricio - March

09 Mar 2026

Contributed by Lukas

Once a month we'll be dropping into the feed with a (totally optional) prompt for listener submissions. This month Mauricio is thinking about navigati...

Will I feel guilty if I choose not to freeze my eggs?

16 Feb 2026

Contributed by Lukas

Through Bunny's husband's job, she has access to one free round of IVF. They've recently started talking to fertility clinics, but she's not quite re...

A Prompt from Mauricio - February

11 Feb 2026

Contributed by Lukas

Once a month we'll be dropping into the feed with a (totally optional) prompt for listener submissions. This month Mauricio is thinking about power i...

How do I trust myself?

19 Jan 2026

Contributed by Lukas

Lucy has lived in many different cities, but grew up in New York and has recently moved back. She's starting to feel at home, and would love to stay r...

Looking Forward, Looking Back: A 2025 Reflection (with Mauricio and Vanessa)

22 Dec 2025

Contributed by Lukas

Mauricio Bruce has been the host of The Real Question for a full year! This week he's joined by Vanessa Zoltan to talk about hosting the show and what...

Did They: Re-Apply to Medical School?

20 Dec 2025

Contributed by Lukas

As we end our year of 'Should I?' questions, we're checking back in with some past guests. How did things turn out for them? Did they make a final dec...

Did They: Quit Keeping Kosher?

19 Dec 2025

Contributed by Lukas

As we end our year of 'Should I?' questions, we're checking back in with some past guests. How did things turn out for them? Did they make a final dec...

Did They: Invite Their Dad to Their Wedding?

18 Dec 2025

Contributed by Lukas

As we end our year of 'Should I?' questions, we're checking back in with some past guests. How did things turn out for them? Did they make a final dec...

Did They: Change the Way They Talk About Their Health?

17 Dec 2025

Contributed by Lukas

As we end our year of 'Should I?' questions, we're checking back in with some past guests. How did things turn out for them? Did they make a final dec...

Did They: Decide to Have a Child?

15 Dec 2025

Contributed by Lukas

As we end our year of 'Should I?' questions, we're checking back in with some past guests. How did things turn out for them? Did they make a final dec...

Should I: Try to Make More Friends?

08 Dec 2025

Contributed by Lukas

Erika is an introvert and she’s struggled with friendship in the past. Sometimes people she thought were her friends, didn’t feel the same way abo...

Should I: Research My Family History?

01 Dec 2025

Contributed by Lukas

Alex's mom was adopted and has chosen not to look into her biological roots. But as Alex begins her own search into family history, she has her own qu...

Should I: Try to Get Pregnant Now?

24 Nov 2025

Contributed by Lukas

Marie and her partner know they want kids and now seems like a optimal time to try. They have really good parental leave in their current jobs. Marie'...

Should I: Stop Working with My Friends?

17 Nov 2025

Contributed by Lukas

This week’s guest is an artist whose work relies on close collaboration with friends. But those friends don’t share the same professional ambition...

Should I: Plan to Take Care of My Parents in the Future?

10 Nov 2025

Contributed by Lukas

César's parents are getting older and as he looks into the future, he's wondering: where does his responsibility to them start and end? How much shou...

Should I: Dye My Graying Hair?

03 Nov 2025

Contributed by Lukas

Rebecca always knew her hair would change, she just didn't think it would happen now, in her 30s. She's been on a long journey to accept her curly hai...

Should I: Start Dating?

27 Oct 2025

Contributed by Lukas

Jackson has built an intentional and fulfilling life for himself. He has a supportive family and many friends, and a career he really enjoys. There ...

Should I: Share Publicly About Experiences with Toxic Workplaces?

20 Oct 2025

Contributed by Lukas

Sruthi works in education. Throughout her career she's has had a wide range of experiences across different institutions – they haven't all been goo...

Introducing: When We All Get to Heaven

15 Oct 2025

Contributed by Lukas

Co-founder of Not Sorry, Ariana Nedelman, has a new podcast project out today! When We All Get to Heaven is a 10-episode series that tells the story o...

Should I: Break-Up with My Partner?

13 Oct 2025

Contributed by Lukas

Our guest today recently moved to be closer to a long distance partner. They thought it would make the relationship feel closer, but since the move, t...

Should I: Leave Vermont?

06 Oct 2025

Contributed by Lukas

Wes and his fiancee are facing one of the classic millennial issues: they can't afford to buy a house. They've lived in Vermont all their adult lives ...

Should I: Write a Nicer Email to an Ex-Friend? (with Vanessa Zoltan)

29 Sep 2025

Contributed by Lukas

About three years ago, Vanessa "broke-up" with one of her close friends. She tried to do it kindly, but in retrospect she feels guilty for how it all ...

Should I: Give Theater a Second Chance?

22 Sep 2025

Contributed by Lukas

When Katy was a kid, she dreamt of being a stage actress. After some early rejections, she pivoted to stand-up and improv and built a career for herse...

Should I: Give Up on My Album?

15 Sep 2025

Contributed by Lukas

Naomi Westwater released their latest album, Cycle & Change, this past spring. This album release intersected with a lot of big life events – a ...

Should I: Reach Out to a Friend Who Ghosted Me?

08 Sep 2025

Contributed by Lukas

Five years ago, Karolina's friend stopped replying to her messages. Karolina doesn't know why. Did she do something wrong? Was the friend just going t...

Should I: Start Saying No to Opportunities?

01 Sep 2025

Contributed by Lukas

Christine Flynn calls herself 'a bit of a workaholic.' She's always taking on new projects and managing some aspect of life with a successful career, ...

Should I: Apply to Medical School Again?

25 Aug 2025

Contributed by Lukas

Sarah has been on the path to medical school for the past few years – she's taught herself physics and chemistry, she's taken the MCAT and done...

Should I: Try to Reconnect with my In-Laws?

18 Aug 2025

Contributed by Lukas

About two years ago, Brandice and her husband decided to limit contact with her in-laws after one of their children came out as trans. The in-laws cou...

Should I: Date After Divorce?

11 Aug 2025

Contributed by Lukas

Melissa has two big things going on in her life: she's getting a divorce from her husband and she's recently realized she's bisexual. As she thinks ab...

Should I: Move to Avoid Climate Disaster?

04 Aug 2025

Contributed by Lukas

Sophie loves her home in the village. She's surrounded by nature and she feels like she can be herself. But with climate events on the rise, is it wis...

Should I: Re-Apply to Medical School?

28 Jul 2025

Contributed by Lukas

Clinton applied to medical school five times after graduating college. He never got in and eventually resigned himself to that reality. And he's been ...

Should I: Come Out to My Family?

21 Jul 2025

Contributed by Lukas

This week’s guest is anonymous—but their question is one many people wrestle with: Should I come out to my family? Their family is conservative an...

Should I: Quit My Job?

14 Jul 2025

Contributed by Lukas

Hallie has started to notice a pattern in her life: once she gets a year and a half into a job, she feels the urge to 'job hop' – to quit and move o...

Should I: Talk to My Cousin About Theology?

07 Jul 2025

Contributed by Lukas

Bailey—an ordained minister in a progressive church—recently got married. But their conservative Christian cousin didn’t attend the wedding, cit...

Should I: Change my Relationship to Making Music?

30 Jun 2025

Contributed by Lukas

Sophie has been a songwriter ever since she was 12 years old. She put out her first album when she was 16 years old. But as she's gotten older, she's ...

The Practice of Re-Enchantment (with Brooke Williams)

23 Jun 2025

Contributed by Lukas

Today we’re breaking our normal format to speak with Brooke Williams, the author of Encountering Dragonfly: Notes on the Practice of Re-Enchantment....

Should I: Get a Preventative Mastectomy?

16 Jun 2025

Contributed by Lukas

Elyse's mom died of breast cancer a few years ago. Recently, she's tested positive for the same cancer-causing gene that her mom had. That puts her at...

Should I: Stop Doing People Favors?

09 Jun 2025

Contributed by Lukas

Jolie Doggett struggles with boundaries. She's a classic 'yes' person – when someone asks her to jump, she says "how high?" She knows this abou...

Should I: Let My Parents Buy Me a Flat?

05 Jun 2025

Contributed by Lukas

Stefanie and her parents have never quite seen eye-to-eye about the best way to live. Stefanie has sought passion and spontaneity. Stefanie's parents ...

Should I: Care Less About Work?

26 May 2025

Contributed by Lukas

Theodora is starting law school in the fall and she's nervous about the workload and intensity. She's a hard worker and she's worried that she'll get ...

Should I: Quit Keeping Kosher?

19 May 2025

Contributed by Lukas

Gillian doesn't eat pork and doesn't eat shellfish. It's her version of keeping kosher and she's been doing it for the past decade. Recently, however,...

Should You: Get a Divorce?

12 May 2025

Contributed by Lukas

This week we have a special episode on the topic of divorce. Vanessa calls her friend, couples and family therapist Colette Potts, to discuss common i...

Should I: Remain Childless?

05 May 2025

Contributed by Lukas

There's certainly been a theme with our submissions lately! Just like our guest from Should I: Have a Child?, Emily feels pulled in two directions abo...

Should I: Expand My Business?

28 Apr 2025

Contributed by Lukas

Brandon runs a successful restaurant group with his husband. Things are stressful, it’s a lot to manage, and they just got a great offer to open ano...

Should I: Invite My Dad to My Wedding?

21 Apr 2025

Contributed by Lukas

Natalie has been ‘low-contact’ with her dad for a while now – she doesn't reach out or put any effort into the relationship, but hasn'...

Should I: Change The Way I Talk About My Health?

14 Apr 2025

Contributed by Lukas

In the course of Sarah’s life, she often finds that she has to talk about her migraines. But the reactions she gets from people are frustrating and ...

Should I: Have a Child?

07 Apr 2025

Contributed by Lukas

Our guest this week has always wanted to have a kid. He’s also aware that having a kid will totally transform his life! Is he willing to give up par...

Should I: Quit Being an Atheist?

31 Mar 2025

Contributed by Lukas

About five years ago, River left Christianity. He felt constrained and needed space to explore and ask questions. Recently, he has been thinking about...

Should I: Continue to Travel to See Family?

24 Mar 2025

Contributed by Lukas

Meghan lives with her partner and daughter in Costa Rica, far away from the rest of their family. They travel frequently to see their family, but it a...

Should I: Quit My Bookclub?

17 Mar 2025

Contributed by Lukas

Elizabeth Rowe's bookclub reading has started to feel like homework. She loves to read, but after a long day of work she wants romance and adventure a...

Should I: Start Charging for My Work?

10 Mar 2025

Contributed by Lukas

Ray is graduating with a Masters of Divinity this year but they know they don't want to pursue a traditional path towards ordination. They do want to ...

Should I: Have a Life Partner?

03 Mar 2025

Contributed by Lukas

Anna knows she wants to be a parent and she doesn't want to do it alone, but she's never particularly wanted a life partner. Should she reconsider tha...

Modern Friendship with Anna Goldfarb

24 Feb 2025

Contributed by Lukas

Anna Goldfarb is a journalist and self-titled 'friendship expert' who is the author of the recent book Modern Friendship: How to Nurture Our Most Valu...

Should I: Settle Down?

17 Feb 2025

Contributed by Lukas

Devon always said that when she moved back to Ohio, she would start planning for the future. She'd think about all the big things: about finding a par...

Should I: Start A Sabbath Ritual?

10 Feb 2025

Contributed by Lukas

Serena, like all of us, wants to spend less time scrolling on her phone. She wants to make more time for community and deep conversations and joy. She...

Should I: Go Back to Church?

03 Feb 2025

Contributed by Lukas

Daniel Schroeder's dad is Methodist minister, so he grew up in the church. But about 10 years ago, after he graduated college, he stopped going. Now, ...

Should I: Change My Checklist for Dating?

27 Jan 2025

Contributed by Lukas

A lot of us have a checklist for dating – things we're specifically looking for (or not looking for) in a partner. After a string of unsuccessful da...

Should I: Marry My Girlfriend?

20 Jan 2025

Contributed by Lukas

Leading up to the election, Marina and their girlfriend started joking about marriage. Once the idea was in the air, the question became more and more...

Should I: Pursue Acting Professionally?

13 Jan 2025

Contributed by Lukas

About a year ago, Evie completed a Master’s course in acting. But actually pursuing acting professionally feels like a whole different thing – lik...

Should I: Take an Art Class in 2025?

06 Jan 2025

Contributed by Lukas

It's a new year and we're bringing you a new season with a new host! Today Mauricio is entertaining a very special guest – Vanessa Zoltan. Maybe you...

Should I Quit: Final Reflection

30 Dec 2024

Contributed by Lukas

That's a wrap on Should I Quit! Today Vanessa shares what she's learned over the past two years of making this show. In exactly a week we'll be back w...

Did They Quit: Being a Stay-at-Home Parent?

28 Dec 2024

Contributed by Lukas

It's our final 'Did They Quit' of the year! We're wrapping things up with the lovely Sophy. We originally talked to Sophy in April about how her caree...

Did They Quit: Making Political Donations?

27 Dec 2024

Contributed by Lukas

As promised, we're following up today with the other half of Pantsuit Politics: Beth Silvers. Back in March Beth decided she was going to stop making ...

Did They Quit: Cussing

26 Dec 2024

Contributed by Lukas

Today we're checking back in with Sarah Stewart Holland from Pantsuit Politics to find out if she quit cussing. --This show is completely funded by Pa...

Did They Quit: Waiting for a Partner to Have a Baby?

25 Dec 2024

Contributed by Lukas

Merry Christmas and Happy Channukah to those who are celebrating today! Today we're checking back in with Katie, our guest from Should I Quit: Waiting...

Did They Quit: Trying to Date Without the Apps?

24 Dec 2024

Contributed by Lukas

Today, we're checking back-in with Meghan from Should I Quit: Trying to Date Without the Apps?--This show is completely funded by Patreon, and we are ...

Did They Quit: Halifax?

23 Dec 2024

Contributed by Lukas

Before we end 'Should I Quit', we're checking back in with some past guests. How did things turn out for them? Did they quit what they wanted to?Today...

Let's Ask Taylor Swift: Tim McGraw

11 Dec 2024

Contributed by Lukas

Not Sorry has launched its first new podcast since 2020! Let's Ask Taylor Swift is co-hosted by Vanessa and podcaster, writer and ...

Should I Quit: Breastfeeding?

09 Dec 2024

Contributed by Lukas

Julia has three toddlers at home. Her first child stop breastfeeding recently and it was a gradual process of feeling out when he was ready. But with ...

Should I Quit: Being Car-less?

25 Nov 2024

Contributed by Lukas

Zoe was always proud of the fact that she didn't own a car. It reflected her environmentalist values and helped her stay more deeply in community. But...

Should I Quit: Trying to Get a PhD?

11 Nov 2024

Contributed by Lukas

Shannon recently withdrew from her PhD program – with two young kids and a full time job, it wasn't the right time. Now, a few weeks out from t...

Should I Quit: My Ethical Phone?

28 Oct 2024

Contributed by Lukas

Megan believes in doing the ‘right thing’ even when it’s a little inconvenient, so she bought herself an ethical phone. This phone is suppo...

Announcement: New Season Coming Soon

21 Oct 2024

Contributed by Lukas

After two years of Should I Quit?, Vanessa is moving on to other projects. The Real Question is sticking around though, with a brand new host and a ne...

Should I Quit: Trying to Be Close with my Dad?

14 Oct 2024

Contributed by Lukas

Stephanie used to call her dad every day. Then she realized: she was the only one putting work into their relationship. If she stopped calling, they s...

Should I Quit: Befriending Men?

30 Sep 2024

Contributed by Lukas

Andrea keeps having this problem: as soon as her single guy friends get a serious partner, it feels like she can't be close friends with them anymore....

Should I Quit: Buying Home Goods? (with Micaela Blei)

16 Sep 2024

Contributed by Lukas

We're thrilled today to be joined by story-telling coach Micaela Blei – the co-teacher of our upcoming memoir writing class. Micaela enjoys making h...

Should I Quit: Trying to Date Without the Apps?

02 Sep 2024

Contributed by Lukas

Megan has always hated the dating apps. She's tried them – they're awful! Recently, however, she's been wondering if she should suck it up and ...

Should I Quit: Fighting My Acne?

19 Aug 2024

Contributed by Lukas

Hope Rehak has been trying to treat her acne for the last 20 years. She's bought all kinds of things to 'help' – pills, shots, serums, and creams –...

Should I Quit: Wanting to Get Married?

05 Aug 2024

Contributed by Lukas

For most of their life, Kat had a plan: move in with someone, get married, have kids. But recently they’ve been re-evaluating. They live with a long...

Should I Quit: The Plan B for My Radical Life?

22 Jul 2024

Contributed by Lukas

Elizabeth Oldfield wants to live radically in her faith. She wants to transcend traditional ideas of financial stability and community responsibility....

Should I Quit: Buying New Books?

08 Jul 2024

Contributed by Lukas

Charlie James can't stop buying books. Every time they’re in a bookstore, there seems to be a new book calling them, a new trove of knowledge ready ...

Should I Quit: My Relationship with My Mother?

24 Jun 2024

Contributed by Lukas

It’s our last episode with Mauricio Bruce filling in as a guest host! This week on the show, our anonymous guest shares about the difficul...

Special Edition: Storytelling and Taylor Swift (with Margaret H. Willison)

14 Jun 2024

Contributed by Lukas

Vanessa is joined for a small bonus conversation by Margaret H. Willison, faculty on our upcoming Taylor Swift Pilgrimage on Cape Cod. They explore wh...

Should I Quit: Waiting for a Partner to Have a Baby?

10 Jun 2024

Contributed by Lukas

We’re continuing our short series with Mauricio Bruce filling in as a guest host. Mauricio is a transpersonal therapist, chaplain, and the co-leader...

Should I Quit: My City?

27 May 2024

Contributed by Lukas

For the next few weeks on the podcast, while Vanessa is traveling, we have the wonderful Mauricio Bruce filling in as a guest host. Mauricio is a tran...

The Best Advice Show: Deciding with Nell Wulfhart

13 May 2024

Contributed by Lukas

Instead of a regular episode this week, we're sharing an episode of one of our favorite podcasts, The Best Advice Show. Last week, Vanessa had the ple...

Should I Quit: Being a Therapist?

29 Apr 2024

Contributed by Lukas

Kelsie doesn’t always feel good about the work they're doing at their non-profit therapy job – and what’s more, they’re burning themselve...

When to Quit Thinking About a Problem (with Mauricio Bruce)

15 Apr 2024

Contributed by Lukas

Mauricio Bruce is a transpersonal therapist, chaplain, and the co-leader of our What Matters program. This week he joins Vanessa to talk about visuali...

Should I Quit: Being a Stay-at-Home Parent?

01 Apr 2024

Contributed by Lukas

Sophie decided to take some time off work when she had her second child, but she always thought she would go back to her career in law. Since then how...

Should I Quit: Making Political Donations? (with Beth Silvers)

18 Mar 2024

Contributed by Lukas

A few weeks ago we had on Sarah Stewart Holland of Pantsuit Politics and today we're joined by her brilliant co-host, Beth Silvers. Beth makes small d...

Bonus Conversation: How We Misunderstand Homelessness with Charyti Reiter

14 Mar 2024

Contributed by Lukas

For our annual fundraiser at Not Sorry, we are again supporting the wonderful organization On The Rise. On The Rise’s work begins with individuals e...

Should I Quit: Halifax?

04 Mar 2024

Contributed by Lukas

Kaitlyn and her partner moved from Winnipeg to Halifax three years, excited to start a new life in a beautiful city. But three years later, they're st...

Should I Quit: My Personal Bank Account?

19 Feb 2024

Contributed by Lukas

When Anisa and her husband got married, they mostly merged their finances – all except one little bank account that Anisa keeps on the side. Seven y...

When to Quit Trying to Get Published (with Mackenzi Lee)

05 Feb 2024

Contributed by Lukas

Mackenzi Lee is a New York Times bestselling author and the teacher of our upcoming Publishing Crash Course. This week she joins Vanessa to talk about...

Should I Quit: Cussing? (with Sarah Stewart Holland)

22 Jan 2024

Contributed by Lukas

We're thrilled today to be joined by Sarah Stewart Holland, co-host of Pantsuit Politics. Sarah was raised in a no-cussing household. When she got old...

Should I Quit: The Idea of Having Kids?

08 Jan 2024

Contributed by Lukas

When Lizzy was younger she always wanted kids. Over time, however, as the realities of life have crept in, she has started to feel more conflicted. No...

Should I Quit: End of Year Reflection

29 Dec 2023

Contributed by Lukas

Vanessa is joined by our Should I Quit? producer, Ariana, in our final episode of 2023. Together they look back at the past year of the show and share...

Did They Quit: Their Relationship?

28 Dec 2023

Contributed by Lukas

In our final guest conversation of the season, we check back in with Emily from Should I Quit: My Relationship? We hear from Emily about the status of...

Did They Quit: Trying to Get Better?

27 Dec 2023

Contributed by Lukas

We're back with another Should I Quit follow-up! Today we're chatting with Fran, who was the guest on one of our first episodes this year. We hear fro...