The Bittersweet Life

Latest Episodes:

Bittersweet Moment #216: The Route of the Seven Churches Jan 22, 2025

Show notes

What does it mean to do the Giro delle Sette Chiese, or the Route of the Seven Churches? And what does it have to do with Rome's newly inaugurated Jubilee?

Find out on this all-new mini-episode! Plus, learn some fun facts about Rome's seven most important churches!

To find out more about Rome's Jubilee, don't miss our previous mini-episode, Bittersweet Moment #215: Rome's Jubilee Arrives!

And don't miss your chance to visit Rome with us, on our intimate Rome listener trip, coming up in October 2025. Find out all about it here, or email us for more information!

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COME TO ROME WITH US: For the third year in a row, we are hosting an intimate group of listeners for a magical and unforgettable week in Rome, this October 2025! Discover the city with us as your guides, seeing a side to Rome tourists almost never see. Find out more here.

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JOIN THE CONVERSATION: If you have a question or a topic you want us to address, send us an email here. You can also connect to us through Twitter, Facebook, and Instagram. Tag #thebittersweetlife with your expat story for a chance to be featured!

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

Episode 568: The Benefits and Dangers of Being Stubborn Jan 20, 2025

Show notes

Is being stubborn a good thing or a bad thing?

Tiffany has always considered it one of her best qualities, but after listening to last week's expat interview with Darlene Sullivan, now she's not so sure.

Katy and Tiffany discuss their takeaways from the previous episode, and Tiffany shares a story about the time being stubborn definitely did not benefit her.

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ADVERTISE WITH US: Reach expats, future expats, and travelers all over the world. Send us an email to get the conversation started.

BECOME A PATRON: Pledge your monthly support of The Bittersweet Life and receive awesome prizes in return for your generosity! Visit our Patreon site to find out more.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

[THE BITTERSWEET PAST] Hitting an Expat Plateau Jan 17, 2025

Show notes

This week's episode is inspired by a letter from one of our long-time listeners. Giovanna wonders what to do after hitting an "expat plateau," when the rapid learning and expanding period of being a new expat inevitably slows down.

After a little over a year living on the idyllic Italian island of Ischia (by way of New York, London, and Rome), Giovanna ponders what to do when the novelty of expat life wears off and you're left with just... life.

She also asks the question: does moving to the tiny Italian town where her mom was born somehow nullify the life her parents strived to create as immigrants in the States?

We explore this and other topics on this episode pulled from our archives.

***The Bittersweet life podcast has been on the air for an impressive 10+ years! In order to help newer listeners discover some of our earlier episodes, every Friday we are now airing an episode from our vast archives! Enjoy!***

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ADVERTISE WITH US: Reach expats, future expats, and travelers all over the world. Send us an email to get the conversation started.

BECOME A PATRON: Pledge your monthly support of The Bittersweet Life and receive awesome prizes in return for your generosity! Visit our Patreon site to find out more.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

[PATREON PREVIEW] Disaster and Loss in LA Jan 15, 2025

Show notes

On this week's exlusive bonus episode, we talk about the catastrophic fires that are, as of recording time, still raging in the Los Angeles area, and how they are affecting some of Tiffany's closest family members.

Want to hear more?

Become part of the Bittersweet Life community by supporting just on Patreon! For as little as $5 per month—less than the price of a coffee in some places—you will have access to multiple bonus episodes every single month.

You'll hear conversations that would never take place on the main show, you'll be part of our new chat community, you'll have access to Patreon-only content in addition to bonus episodes, and you'll be invited to join us for regular live meet-ups.

But most importantly, you'll be doing your part to help keep this show alive—an independent podcast with no corporate support. (You'll also help keep it virtually ad-free!)

Check our our Patreon page for all the details, and consider joining us at the $5 level or above. We are eternally grateful!

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ADVERTISE WITH US: Reach expats, future expats, and travelers all over the world. Send us an email to get the conversation started.

BECOME A PATRON: Pledge your monthly support of The Bittersweet Life and receive awesome prizes in return for your generosity! Visit our Patreon site to find out more.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

Episode 567: What if Moving Abroad Isn't Great? (with Darlene Sullivan) Jan 13, 2025

Show notes

You've dreamed of moving to Italy since you were 16 years old, and after years of scheming and planning, you finally made it happen.

But... you're not happy.

Could it be that you made a mistake in moving abroad? Or maybe you're just not in the right town.

Longtime listener Darlene Sullivan joins us this week to talk about what happens when expat reality doesn't quite live up to your dreams—but how that doesn't necessarily mean you've made a mistake. Sometimes you just need to recalibrate and find a living situation that matches your personality.

Another important lesson: don't underestimate how trauma might be souring your expat experience. Just because something bad happens in your adopted country, doesn't mean you're not supposed to be there.

If you haven't already, go back and listen to our first interview with Darlene, shortly after her move to Bolzano, Italy back in 2020, Episode 435: When Expat Dreams Come True.

Darlene is a freelance textile designer. Find her work at her website. Or find her on Instagram here. If you're interested in reading her Master's thesis, Flocking Together, which she mentions in the episode, it's available here.

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ADVERTISE WITH US: Reach expats, future expats, and travelers all over the world. Send us an email to get the conversation started.

BECOME A PATRON: Pledge your monthly support of The Bittersweet Life and receive awesome prizes in return for your generosity! Visit our Patreon site to find out more.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

[THE BITTERSWEET PAST] Living Life in a Foreign Language Jan 10, 2025

Show notes

Have you ever wondered how speaking a second or third language more often than your native tongue can reshape your thinking?

In this episode from the archives of The Bittersweet Life, Tiffany reflects on 15 years of living abroad and how it has transformed the way she communicates—even in her first language.

We dive into the surprising cognitive and emotional challenges of navigating life in a foreign language, especially for writers, who rely so heavily on nuanced expression.

Plus, we explore how bilingual or multilingual couples often gravitate toward one shared language in their relationship—and how this dynamic might shift dramatically when raising a child in a multilingual household.

Tune in to discover the fascinating ways language shapes identity, relationships, and the thought-process.

Language is one of our most popular topics! You might be interested in these past episodes about language:

Episode 476 Italy Bans the English Language

Episode 430 Does Language Shape Thinking?

Episode 355 Losing Language

Episode 63 LANGUAGE, Part 3 (with J J Michael)

Episode 19 LANGUAGE, Part 2

Episode 2 LANGUAGE, Part 1

Bittersweet Moment #96: Disappearing Languages

Bittersweet Moment #54: Learning to Read in Two Languages at Once

Bittersweet Moment #3: LANGUAGE

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ADVERTISE WITH US: Reach expats, future expats, and travelers all over the world. Send us an email to get the conversation started.

BECOME A PATRON: Pledge your monthly support of The Bittersweet Life and receive awesome prizes in return for your generosity! Visit our Patreon site to find out more.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

Bittersweet Moment #215: Rome's Jubilee Arrives! Jan 08, 2025

Show notes

Rome's Jubilee is here!

And our Bittersweet Moments are back! (And you thought Christmas was over.)

On this short-but-sweet mid-week mini-episode, Tiffany explains the history and origins of this very Roman and VERY Catholic event, why it's so important, and what to do if you want to take part in this historic pilgrimage.

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ADVERTISE WITH US: Reach expats, future expats, and travelers all over the world. Send us an email to get the conversation started.

BECOME A PATRON: Pledge your monthly support of The Bittersweet Life and receive awesome prizes in return for your generosity! Visit our Patreon site to find out more.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

Episode 566: How to Move to Italy (with Thea Duncan) Jan 06, 2025

Show notes

So you want to move to Italy but... HOW???

Today we are joined by a guest who happens to have all the answers.

Thea Duncan is the self-described "fairy godmother to people's dolce vita dreams." She's the founder of Doing Italy, where she and her team help people gain the knowledge and resources they need to move to Italy as well as buy property in Italy with ease, all while avoiding many of the pitfalls that negatively affect other expats when moving abroad.

She answers all our questions, including: Is it really true that you can buy an Italian villa for $1?

And, what is the thing most people get wrong when attempting their big move?

As well as the most basic: what are the easiest ways to move to Italy legally?

If moving to Italy is a dream for you, don't miss this interview!

Find Thea at her webite, or on Facebook or Instagram.

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ADVERTISE WITH US: Reach expats, future expats, and travelers all over the world. Send us an email to get the conversation started.

BECOME A PATRON: Pledge your monthly support of The Bittersweet Life and receive awesome prizes in return for your generosity! Visit our Patreon site to find out more.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

Episode 565: Resolutions Old, Resolutions New Dec 30, 2024

Show notes

It's that time of year again!

Every turn of the year, we look back at the resolutions we set for the previous year and discuss whether or not we accomplished them, or at least got close. This is often a very cringe-worthy exercise.

Undaunted by any failures, we also set resolutions for the coming year.

Don't miss this fun annual tradition!

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ADVERTISE WITH US: Reach expats, future expats, and travelers all over the world. Send us an email to get the conversation started.

BECOME A PATRON: Pledge your monthly support of The Bittersweet Life and receive awesome prizes in return for your generosity! Visit our Patreon site to find out more.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

Episode 564: An Ever-Changing Holiday Dec 23, 2024

Show notes

How much has Italian Christmas changed over the years?

Turns out, even in the last ten years, since we began this show, the way Italians celebrate Christmas has evolved. We listen back to one of our very first episodes, when we discussed Katy's first (and only) Christmas in Italy back in 2013. How did it feel different to her from Christmas in the States, and what makes an expat Christmas different from one in your home country?

Listening back, Tiffany observes how different Christmas in Italy feels only ten years later.

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ADVERTISE WITH US: Reach expats, future expats, and travelers all over the world. Send us an email to get the conversation started.

BECOME A PATRON: Pledge your monthly support of The Bittersweet Life and receive awesome prizes in return for your generosity! Visit our Patreon site to find out more.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

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