Dating Disasters and Life Lessons: A 20-Year Friendship Built on Travel Stories
Listen, I've had my share of questionable travel decisions—like that time I quit my job to start a travel business or when I thought bringing my border collies to a group trip planning session was a good idea. But my friend Tamara? She's collected international dating disasters like I collect passport stamps, and somehow turned it into an art form.
Tamara and I met over 20 years ago as camp counselors for EF Tours in Long Beach, California. In what can only be described as cosmic intervention, we got randomly paired as roommates and have been best friends ever since. Back then, we were working for a group travel company, blissfully unaware that we'd both end up as serial solo travelers with enough dating horror stories to fuel a Netflix series.
Tamara exploring the American southwest.
When Your Mom Gives You Wings (Literally)
Tamara's travel DNA comes courtesy of her flight attendant mother, who apparently had the best job perk ever: greeting couples emerging from airplane bathrooms with champagne and a "Welcome to the Mile High Club" toast. I mean, can you imagine? Talk about job dedication.
But here's where the story gets real: After losing both parents at a young age, Tamara had an epiphany in the bathtub (as one does) and decided to quit her job, sell everything, and travel the world for a year. Her plan? Visit 24 countries in 12 months while spreading her mother's ashes in each destination.
Spoiler alert: Traveling internationally with a bottle of what looks suspiciously like sand raises some eyebrows at airport security. Picture this scene in Costa Rica—security guards asking "¿Qué es eso?" while Tamara frantically tries to explain in broken Spanish that it's "mi madre." The confusion that followed was both heartbreaking and hilarious, especially when she forgot how to say "dead" and ended up saying her mother was "no more."
Golden hour hits different when you’re on a boat.
The Italian Stallion (Who Wasn't)
But let's talk about Luca. Oh, Luca. This is the travel romance story that makes my worst dating disasters look like fairy tales.
Tamara met this Italian bed-and-breakfast owner on the gorgeous island of Elba (where Napoleon was exiled, which should have been a red flag). Luca was tall, hot, chivalrous—basically straight out of central casting for "Italian Romance Novel Hero." After an on-again, off-again long-distance situation, he invited her back to Italy with promises of figuring out their future together.
Here's what he promised: a romantic Italian getaway where he'd take care of everything.
Here's what she got: abandoned in a cottage on a cliff with no WiFi, no food, no money, and a boyfriend who disappeared 80% of the time. It was like Rapunzel, but with better scenery and significantly worse Wi-Fi.
The kicker? When she told him it wasn't working out, he had the audacity to ask if she thought they had a future. Sir, you left her stranded on a mountain with no snacks. What future?
But wait, it gets better. A year later, Luca texted her a hospital photo explaining he'd hit a wild boar with his scooter and was now in a wheelchair. His solution? Maybe she'd like to come back to Italy to take care of him. The man who couldn't be bothered to feed her when she visited wanted her to return as his personal nurse. The audacity is truly breathtaking.
Tamara on her marathon of seeing the world—one country at a time!
The Real Lessons Hidden in the Chaos
Beyond the entertainment value of these stories, Tamara dropped some serious wisdom about dating while traveling:
Practice not being attached to outcomes. When you're traveling, you can't plan your wedding on the first date because you literally don't know how long you'll be in town. This forces you to stay present and enjoy experiences for what they are.
Locals make the best tour guides. Some of her most incredible travel experiences happened because she met people who showed her places she never would have discovered on her own—like camping by a river in Israel or exploring hidden spots that don't make it into guidebooks.
Safety isn't negotiable. Watch your alcohol intake, share your location, and trust your gut. Getting blackout drunk with strangers in foreign countries isn't "living your best life"—it's playing Russian roulette with your safety.
From Disasters to Happily Ever After
Here's the plot twist: after years of dating internationally and collecting stories that would make even reality TV producers blush, Tamara found love with someone completely opposite to her usual type. He's a rule-follower; she's a rule-breaker. But somehow, they work.
Her advice for anyone still looking for love? Fix yourself first. "Would you date you?" she asked, and honestly, that question hit different. She had to examine her own patterns, unrealistic expectations, and the energy she was bringing to relationships.
And maybe give people more than one date to prove themselves. Shocking concept, I know.
The Bottom Line
Travel dating isn't about finding your soulmate in every city (though it could happen). It's about staying open to experiences, learning about yourself, and collecting stories that will make your friends both laugh and cringe for decades to come.
Sure, you might end up abandoned on an Italian cliff or explaining your mother's ashes to confused security guards. But you'll also discover hidden corners of the world, practice being present, and maybe learn something about what you actually want in a partner.
Just remember: if someone invites you to their private island cottage, make sure there's food, Wi-Fi, and an escape plan. Trust me on this one.
Tamara is a lifelong child and youth advocate, rescue animal lover, and storyteller with a passport full of stamps. Daughter to a flight attendant, Tamara spent her weekends as a child travelling to overseas countries, accompanying her mother to work when she couldn't find child care. Born and raised in beautiful, Vancouver Canada, Tamara has travelled to 39 countries, 24 of those countries being travelled to in under a year. She currently resides downtown, Vancouver with her rescue dog and cat, Ireland and Africa and she spends most of her time planning more trips and hiking with her boyfriend.
