The Great Italian Shopping Spree (Or: How Lufthansa Accidentally Funded Our Engagement Wardrobe)
Every proposal story should have a fun backstory. Ours came courtesy of Lufthansa, who managed to lose every single bag we owned on the way to Italy — and then didn’t give them back until the trip was basically over.
The ring, thankfully, was in my carry-on. That was the one thing I wasn’t about to trust to a baggage carousel.
Touchdown, No Bags
We landed, waited at the carousel, watched it slow down and eventually stop, and accepted the truth: our suitcases were somewhere else on the planet. Not delayed by a day. Not delayed by two days. Gone for the entire trip. Ski clothes, everyday clothes, ski gear, our carefully packed outfits for what was supposed to be a very special couple of weeks — all of it, missing.
Lufthansa’s answer was simple: go buy what you need, keep the receipts, and they’d sort out reimbursement later. So that’s exactly what we did. In hindsight, “go buy what you need” is a dangerous sentence to say to two people in Italy.
Florence: Round One
Florence was our first stop, and our first taste of building an entire wardrobe from scratch in a city that is, frankly, one of the worst possible places to try to shop responsibly. Every rack we walked past was better than the last. What started as “let’s just get basics to get through the next few days” turned into a genuine spree — real clothes, real shoes, real everything, because we genuinely had nothing else to wear.
Ortisei: The Ski Gear Chapter
From Florence we headed up into the Dolomites to Ortisei — this tiny, impossibly charming mountain town that’s basically Italy’s answer to Aspen. Cobblestone streets, alpine chalets, world-class skiing right outside the door, and us with zero ski gear to our names.
So the spree continued, except now it had a new category: skiwear, ski gear, and ski passes, all purchased at altitude, all purchased under duress. Jackets, base layers, gloves, goggles — the full kit, bought twice in one trip because our actual gear was still MIA somewhere in an airport system that had apparently forgotten it existed.
By the time it was all said and done, we’d each racked up around $5,000 in “emergency” purchases. Which is a genuinely wild number to say out loud, but when you need to ski, dress, and generally exist for two weeks with nothing but a passport and a proposal ring, the math adds up fast.
The Twist: The Bags Show Up Right at the End
Naturally, our actual luggage reappeared just as the trip was wrapping up — perfect timing to be functionally useless, but great timing for symmetry in a blog post. We flew home with two full wardrobes: the one we packed, and the one Italy sold us.
The Real Plot Twist: Fighting Lufthansa With AI
Getting the money back is its own story. Instead of the usual slog of hold music and copy-paste customer service emails, we leaned on AI to write and manage the entire reimbursement battle — every email, every follow-up, every “per my last message” moment. It worked. We got fully reimbursed for the shopping spree.
Flights were their own separate fight. Kari came out on top and got her flight fully refunded, while I landed a 50% refund on mine — which either says something about negotiation, luck, or the mysterious internal logic of airline compensation policies. Probably all three.
Florence
Dolomites
Food
Proposal
