The Bittersweet Life – Details, episodes & analysis

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.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

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.

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!

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.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

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.

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!

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.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

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.

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!

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.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

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.

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!

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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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. 

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.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

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.

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!

Continuing our month-long look back at life during the initial outbreak of the Covid-19 pandemic, we are re-airing Part 2 of our peek into our lives—and the lives of our listeners all around the world—while we live under the restrictions of our various countires.

Katy offers a rare glimpse into what it’s like to edit and a long piece of tape, extracting its gems to transform it into something engaging.

Karen, a US expat in the Dolomites, cycles home from work, hoping not to be stopped by the Carabinieri. Jill in Oregon spots a hummingbird and looks for the silver lining in the midst of chaos.

From Steve and Linda in Orvieto making homemade pizza, to Simon from Melbourne as he walks his dog, to Valentina in Trentino counting her blessings via social media. Lastly, take a peek into Katy and her husband Derek’s craft night in Seattle.

We end this show with the song Six Feet Apart, sent in by Seattle artists Miles and Katrina, and inspired by the social isolation of the coronavirus pandemic. 

Find Part 1 of this episode here.

***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!***

-------------------------------------

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.

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.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

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.

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!

Who remembers what life felt like during the first wave of the Covid-19 pandemic, when cities and entire countries were shutting down right and left? Believe it or not, it all started five years ago this month! So we are digging back into our archives to bring you episodes from that momentous time all month long.

On this episode, which originally aired on April 5th 2020, we ask our listeners:

What does a day in the life of someone under lockdown look like? And they responded, offering a peek into their lives throughout the course of a day. We also offer our own. 

From Lynn in San Francisco as she studies Italian to Scott trying to find some space for himself in his basement, from Madeline in Menlo Park remembering to be thankful to best-selling author Jess Walter who is very used to working from home.

From Nancy in Wisconsin dealing with spring snowfall to Theresa in Port Townsend in a hailstorm to Jill in Manhattan, where the only sound on the city streets is the chirping of birds, and many, many others.

We got so many glimpses into the lives of our diverse listeners that we had to divide this episode into two parts. But don’t fret—the second part is available here.

***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!***

-------------------------------------

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.

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.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

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.

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!

Katy moved to Rome once. Does that mean she'd be brave enough to do it again? Are you brave enough to move to a brand new city? What about a brand-new country?

Katy and Tiffany use a listener email to kick off this episode from our archives.

If you like this topic, don't miss Part 1 of this episode!

***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!***

-------------------------------------

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.

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.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

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.

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!

On this Bittersweet Moment, taken from our archives, Tiffany and Aurelio chat about their recent visit to one of Rome’s most secret and best-hidden gems: the Tempietto of Bramante.

Find out what makes this minuscule “temple” so utterly sublime, which ancient temple it was inspired by, and which domes around the world have been inspired by it.

Aurelio also chimes in about his favorite thing about visiting the Tempietto. (Hint: it rhymes with Tempietto but begins with C-O-R-N.)

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.

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.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

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.

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!

Have you ever lost your mind over a foreign language?

This week's guest, Melissa Muldoon, did just that over 15 years ago, when she dove head first into studying the Italian language. She was so crazy about Italian in fact, that she dubbed herself the "Studentessa Matta" (crazy student) and started blogging about her Italian-learning journey... in Italian.

What began as a blog to flex her Italian writing skills has turned into a career as an Italian language teacher and coach, an Italian cultural ambassador, an author of historical fiction set in Italy, and a leader of immersive language and culture trips to Italy, which she hosts twice a year.

Melissa joins us to talk about her journey to learn Italian, what made her go "crazy" for it, and—perhaps most valuably—how she manages to incorporate the Italian language into her daily life without actually living in Italy.

Find out more about Melissa's trips and language programs at her website, buy one of her works of historical fiction, or follow her on Instagram or Facebook.

-------------------------------------

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.

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.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

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.

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!