The Bittersweet Life

Lots of Americans move abroad to a lower-cost-of-living country in hopes of making their salary stretch further. And if they manage to continue earning an American salary from abroad (even a modest one), they can go on to lead prosperous and comfortable lives far beyond what would be possible in the States.

But what happens when they decide it's time to move home?

A recent article in the New York Times, They Went Abroad to Save Money. Moving Back Seems Unaffordable looks at this conundrum, and we continue the discussion by musing on the article...

On this episode from our archives, we tell a true story of corruption, evil, and avarice...

A powerful, unscrupulous man whose two greatest vices are greed and lust. He's close to his family...perhaps too close (particularly his daughter). He has many children by different women, but the three he loves most are two sons and a daughter...a beautiful blond-haired daughter.

He holds a position of great power, although the machinations he employed to get it are mired in scandal. Bribery was most certainly involved—and perhaps even blackmail.

He is resented by...

Tiffany's household has been shaken up by a surprising new family member. What do you think? Are you surprised?

This is just a sneak peek of a much longer bonus episode that drops today, available exclusively to our generous Patreon supporters.

Want to hear the whole episode and many many more like it?

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.

...

When you leave your home country and move abroad as a young person, you probably have a plan for finding a place to live, securing employment, maybe even getting health insurance.

But what about when it comes to finding love?

Dating offers unique challenges to expats, who often have a hard time communicating or even just being themselves in a foreign language, understanding local dating "rules," and adapting to cultural norms that can often be totally foreign.

Today's guest Maddalena Vario experienced this for the first time when she moved from Puglia, Italy...

In this episode from our archives, we chat with expat, author, and vlogger Dana Newman, an American living in Germany. Dana moved to Europe back in 2008, first to Prague, then later to Munich, where she married a German and still lives today.

On her YouTube channel, Wanted Adventure, Dana talks about her experiences living abroad in general and living in Germany in particular, including the culture, the food, the traditions, and, of course, mastering the German language. (The infamously difficult-to-learn German language! Do you know how many ways there are to say "the" in German? We don't...

When an unpleasant hitch seems to ruin your best-laid plans, sometimes, just sometimes, you discover later that it was all for the best. That something better than you could have ever imagined was in store for you.

In fact, sometimes these "happy accidents" can lead to amazing outcomes, and sometimes even change your life for the better.

On this new episode, we talk about the happy accidents we've experienced in our lives and how we never saw them coming.

Write to us here (or send us a voice memo...

What do Goethe, Ernest Hemingway, Pablo Picasso, Paul Gauguin and so many other writers and artists have in common? They all reached the apex of their creative output while living outside their countries of birth.

An email from a listener, who also happens to be a member of indie band Trash Can Dream, inspired this episode from our archives. Emma Grace Stephenson is one of two Aussie expats who make up the band that is now based in New York City. Her email sparked a discussion on how travel, and specifically living abroad, can inspire art and...

Tiffany lays out five reasons why you should drop whatever you're doing and come spend a week in Rome with us this fall... and why it might just be your best trip ever!

Thinking of joining us on our intimate Rome listener trip in November 2026? Find out all about it here, or email us for more information!

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COME TO ROME WITH US: Our third annual Bittersweet Life Roman Adventure is in the books! If you'd like to join us in 2026, and be part of an intimate group of listeners on a magical...

Don't miss this fascinating interview with writer and teacher Victoria Montes, a long-time expat currently living in Guantanamo Bay, Cuba.

Victoria has spent much of her life moving around the word, from Nigeria, Morocco, and Pakistan as a diplomat's kid growing up in the '70s, to a young military police officer based in Germany, to working as a photojournalist covering the war in Afghanistan, and now teaching schoolkids on military bases.

She sits down with us to talk about her journey navigating identity, home, transitions, and the complicated emotions that come with uprooting and...

Some psychologists say that anticipation of a desired event can often bring more happiness than experiencing the event itself. And if that's the case, can we conclude that planning a trip is even more fun that actually taking the trip?

This episode from our archives was inspired by a recent article in the New York Times, Travel and the Art of Anticipation by Stephanie Rosenbloom. We muse about the so-called "happiness reset," the pleasure of anticipating travel, and the joys to be gleaned from reminiscing about past adventures.

***The Bittersweet Life podcast has been on...

Our supporters on Patreon voted YES to this episode idea!

So today we fire up the random question generator again, except this time, there's a twist: we each have to guess what the other person will say.

What does Tiffany wish she learned sooner? Katy answers for her. What natural ability does Katy have? Tiffany has a guess.

Such a fun episode.

This is just a sneak peek of a much longer bonus episode that drops today, available exclusively to our generous Patreon supporters.

Want to hear the whole...

We all have mementos from the past: cards and letters from loved ones, journals from or angst-ridden teenage years, homework from when we were just wee things... but the question is: what do you do with it all?

We can't store an infinite amount of stuff, and how often are we actually going to go back and look at these things?

And yet, these objects often capture memories in a tangible way that simply thinking about them does not. Will we forget the memory without the tangible reminder? And if we do, does that even...

We all have fantasies when we are young about how we want our lives to turn out. Some are far-fetched, some are probably doable.

But do you ever stop to ask yourself how much of life is us trying to fulfill the fantasies of our youth? And what do we do when those fantasies go unfulfilled? Do we look back with regret, or do we just create new ones?

On this episode from our archives, we discuss this topic.

***The Bittersweet Life podcast has been on the air for an impressive 10+ years! In...

What does Easter look like in the most catholic city on Earth? As it turns out, it's all about two things: Jesus, and big chocolate eggs. And I mean BIG.

Hear all about what a traditional Easter is like in Italy on this week's mini-episode.

Don't miss your chance to visit Rome with us, on our intimate Rome listener trip, coming up in October 2026. Find out all about it here, or email us for more information!

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COME TO ROME WITH US: Our third annual Bittersweet Life Roman Adventure is in...

Taxes are enough of a nightmare when you live in your home country. But what happens when you move abroad?

Did you know that the United States is one of only two countries in the world that requires its citizens living outside of the country to file taxes internationally? That mean American expats like Tiffany have to file two returns every year. (Double nightmare!)

Tiffany and Katy talk about their experiences doing their own taxes and whether that is as unwise as it sometimes seems, and Tiffany explains some of the intricacies of filing an...

In this episode from our archives, we explore the topic of hard work vs. luck, when it comes to a person's success.

You did it! You've landed that amazing job, or maybe you're successfully living abroad in the country you've always dreamed of, or you've published your book, bought your dream home, won a major award in your industry (you fill in the blank). The question is: can you chalk it all up to hard work? Or was there some luck involved? And how much of what you've achieved can be attributed to privilege?

It's...

Last week, Tiffany shared two of her favorite childhood movies with her 10-year-old son, and it was almost like stepping back into the past (particularly with one of the films!).

Find out what Aurelio thought of these classic films? Did he love them as much as Tiffany did when she was little?

And how did they stand the test of time?

Most importantly, did re-watching them after so much time make her cry?

This is just a sneak peek of a much longer bonus episode that drops today, available exclusively to...

On this new episode, Tiffany regales us with the beautiful plans she made for a fun weekend that ended up going disastrously awry.

Is part of growing older learning to take such disappointments in stride?

We discuss on this brand-new episode.

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COME TO ROME WITH US: Our third annual Bittersweet Life Roman Adventure is in the books! If you'd like to join us in 2026, and be part of an intimate group of listeners on a magical and unforgettable journey to Rome, discovering the city with us as your guides, find...

In this episode from our archives, we are joined by legendary travel writer Paul Theroux for a candid, backstage interview delving into his five decades spent traveling the world and writing about it.

Paul discusses what brought him to traveling and to writing, and how those two things are inexorably linked, at least for him. He remarks on why he thinks that growing up in a big family helped teach him how to be a good traveler.

He also explains what it means to travel "close to the ground" and offers advice on how to...

On this out-of-the-ordinary mini-episode, Katy digs into some old schoolwork from her childhood. That leads to the question: what should we do with tangible memories from our far-away past, such as old term papers, school presentations, awards, show programs, art projects... these things represent wonderful memories, but they take up so much space.

How do sentimental people learn to let go to all this... stuff? Can we remember a specific moment without any physical reminder of it?

Listen all the way to the end and you might just shed a tear or two.

...

After last week's horror story from Tiffany about her out-and-out war with her upstairs neighbors over her piano playing, we decided to follow up with a more optimistic episode.

Katy has had numerous experiences living in the same apartment building or divided house with friends and she shares her tips and tricks on how to make sharing the walls of a home not only tolerable, but enjoyable!

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COME TO ROME WITH US: Our third annual Bittersweet Life Roman Adventure is in the books! If you'd like to join us in 2026, and be...

In this two-part episode from our archives, Italian expat and cooking expert, Francesca Montillo, joins us for an in-depth interview which inspires us to cook and eat with others daily. She also explains what it is like to grow up in small-town Italy, and move permanently to the United States.

In part two of the episode, the cooking discussion continues. Katy and Tiffany discuss their own cooking habits in response to last week's episode with Francesca Montillo of Lazy Italian Culinary Adventures.

But what happens when Italians express love through food, but you don't like...

This special bonus episode was SUCH fun to create. We hope you laugh along with us as we answer some ridiculous and interesting questions.

This is just a sneak peek of a much longer bonus episode that drops today, available exclusively to our generous Patreon supporters.

Want to hear the whole episode and many many more like it?

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 epis...

What happens when you suddenly develop a passion for playing the piano, and your upstairs neighbors can't stand to hear you playing and take every opportunity to tell you so... but meanwhile their kids are rollerskating over your head at midnight?

A not-so-friendly neighbor war ignites.

Tiffany is in the middle of just one such war, and she regales Katy with all the bitter details on this week's new episode.

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COME TO ROME WITH US: Our third annual Bittersweet Life Roman Adventure is in the books! If you'd like to...

On this episode from our archives, Katy meets up with one of The Bittersweet Life's longtime listeners, San Francisco resident Lynn Fortunato. Lynn is standing on the precipice of change. She's bored of her job, she's not overly attached to San Francisco, her lease is up in September, and she's yearning for something new. But how do you know where you should go—or even if you should go?

One way to get some direction is to consult a psychic medium, someone who has a vision that goes beyond the everyday, perhaps even beyond the realm of th...

You know what no one tells you about moving abroad?

The first year is hard... excruciatingly hard.

Want to make it easier? Follow Tiffany's 7 tips to survive your first year of expat life, laid out on this week's mini-episode.

***Don't miss your chance to visit Rome with us, on our intimate Rome listener trip, coming up in fall of 2026. Find out all about it here, or email us for more information!***

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COME TO ROME WITH US: Our third annual Bittersweet Life Roman Adventure is in the books! If...

Have you ever gotten sick while traveling? Really sick?

Today's special guest, Katy's sister Dana, has and on this possibly TMI episode, she joins Katy and Tiffany to explore the illnesses that you might encounter abroad. And how sometimes, they linger with you longer than you had bargained for.

***Katy's sister Dana (who appears on this episode) has recently been diagnosed with stage 4 agressive brain cancer. To help with the staggering medical costs—her specialist is outside her insurance network—as well of the costs of temporarily relocating to San Francsico for her treatments, please cons...

In this interview from our archives, the executive producer of the Oprah Winfrey Show, Sheri Salata and her cohost Nancy Hala on the popular podcast, The Sheri and Nancy Show join us on this very special episode! Sheri is the author of the new book, The Beautiful No, And Other Tales of Trail, Transcendence, and Transformation.

They discuss the inevitable question that arrives somewhere in your 50s: what's next? In the midst of a major career, an enriching family life, or other successes, how to you find inspiration for your next steps, and more importantly, how to...

Is Katy becoming a curmudgeon? Listen to this recent event, and weigh in!

This is just a sneak peek of a much longer bonus episode that drops today, available exclusively to our generous Patreon supporters.

Want to hear the whole epside and many many more like it?

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 neve...

We all notice some things over other things.

What determines what we notice?

Is it our background? Our innate personality? Our experiences? Our preferences? Our past mistakes? All of these things?

Today we discuss this idea, and chat about the things we notice and why we think we notice them.

What do you think? We always welcome your thoughts and feedback on the topics we discuss. Email us here anytime.

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COME TO ROME WITH US: Our third annual Bittersweet Life Roman Adventure is in the books...

Is the Mona Lisa in the Louvre fake? Was impressionist painter Claude Monet a radical? And was Caravaggio—our show's muse—murdered? Art history holds as many mysteries and baffling stories as it does masterpieces, and Jennifer Dasal, museum curator and host of the wildly popular ArtCurious podcast knows all the best ones.

In this week's episode from our archives, we sit down with Jennifer to chat about her book, ArtCurious: Stories of the Unexpected, Slightly Odd, and Strangely Wonderful in Art History and delve into the fascinating world of mystery and art.

PS Jennifer has...

Don't stumble around one of the most important ancient sites in the world without learning about its incredible history, structure, art, design, and curiosities.

Tiffany is right now putting the finishing touches on an audio tour of the Pantheon, written and narrated by her, and distributed by VoiceMap, an app where real people lead you seamlessly on fascinating audio tours using GPS so you don't even have to look at your phone. (Download VoiceMap for free here.)

After taking a deep, deep dive into the Pantheon's history in preparation for creating this tour, Tiffany learned...

Lately it seems like lots of Americans are moving abroad. But, believe it or not, some American expats are moving back to the States.

Today we're joined by one such ex-expat, or repatriate. Seattle-native Brie Ripley has been on the show before. We first interviewed her back in 2024 after she moved to Rome without ever having been there before. She joined us again about sixe months later, after she had settled in.

And today we sit down with her to talk about why she and her husband decided to move back to the US and...

On this episode from our archives, we give all our listeners a peek into some of the extra bonus content that our Patreon donors are receiving. Every month we offer one or more bonus episodes exclusively for our Patreon supporters, and today we are sharing one of those with our entire audience.

Way back in 2015, we taped a final episode just before Tiffany took a break to have her baby and begin learning the ropes of motherhood. In the second half of the episode, taped several years later, we re-listen to that "before baby" episode and offer...

Most break-ups are painful, but every now and then, they can be fun. Or even funny! Have you had a funny break-up? Tune in to hear ours.

This is just a sneak peek of a much longer bonus episode, available exclusively to our generous Patreon supporters.

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 conv...

February 17th is a big day in Tiffany's life this year... from Martedi Grasso with Aurelio (aka Pulcinella) to her Italian sister-in-law's Master's graduation to her mom's birthday.

Hear Katy and Tiffany chat about what Italian graduation looks like (and what it takes to get your degree) as well as the fun and the surprising (yet very traditional) Carvenale costume Aurelio chose this year.

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COME TO ROME WITH US: Our third annual Bittersweet Life Roman Adventure is in the books! If you'd like to join us in 2026, and be part of an...

What do you do when your partner of almost a decade finally proposes, and after a just few short months of marriage, tells you he thinks you made a mistake getting married?

Well, if you're the guest of this episode from our archives, you pack your bags and start traveling the world. You might never even come back.

On this episode, we sit down with Asia Dawn Simonelli, who's unexpected heartbreak made her realize that life is too short and uncertain to do anything but what brings her joy. Her sudden divorce inspired her to...

On this mini-episode, we talk about one of the most over-looked and underappreciated sites in the entire city. It has it all: glorious medieval mosaics (some of the oldest you'll find in the city), exquisite works of proto-baroque statuary, hidden frescoes that almost no one knows about, and an ancient underground level that ties the history together.

What to know what it is? Listen to this week's Bittersweet Moment and Tiffany will take you there.

And if you want Tiffany and Katy to take you there in person, sign up for our intimate Rome listener...

On the occassion of Valentine's Day, The Bittersweet Life looks at the many different kinds of love, from family love to romantic love to the love you feel for your pets.

Katy sits down with her sisters Dana and Sara to talk about the love that binds them as siblings, and she shares the kind of the love that she feels doesn't get enough credit. She also gets her sisters to open up about their oddest and most inappropriate crushes.

The conversation deepens as they discuss their love for things like birdwatching, the music of...

"All things cute and cuddly" was the surprising topic requested by listener Sara, who supports us at the $50 level on Patreon. Choosing the topic of an episode is just one of many bonuses we offer our Patreon supporters, and as this episode proves, we take that pledge seriously and hold no veto power. The sky is the limit!

In delving into this unexpected topic, we attempt to answer many questions: Why does Tiffany hate cuddly things—and the very word "cuddly" itself? What is the cutest thing Katy ever saw on a plane? And how did the wo...