It all started on the dance floor at Old Crow, a country bar in Chicago. Olivia was in town apartment hunting with her friend Margy when she crossed paths with Nick. Between songs we talked, and by the end of the night, we had exchanged numbers. Over the next month, we got to know each other through text messages and the occasional surprise call from Nick which was just enough to keep Olivia intrigued. When Olivia finally moved to Chicago, Nick invited her to dinner at Twin Anchors so she wouldn't have to worry about cooking after a long day of unpacking. Despite the restaurant being just across the street, Olivia's “time optimism” got the best of her—she walked the wrong way and ended up 35 minutes late. But good things are worth waiting for. That dinner turned into a nearly four-hour date full of laughter, conversation, and an instant connection. From there, one date quickly led to another - whether trying new things around the city or dreaming up future adventures, we found joy in simply being together. Though Olivia hadn’t planned on settling down so soon in a new city, it became clear that this was something special. And the rest, as they say, is history.
After a magical trip to Milan and Bogliasco the year before, Nick had a feeling that Italy would always hold a special place in our story. So when we planned a fall getaway to Florence and Tuscany, he knew it would be the perfect setting to ask one life-changing question. What Olivia didn’t know was that Nick had been hiding the ring for months—and despite a chaotic travel day (including a lost AirPods case and a full carry-on repack at the airport), the ring made it safely across the ocean, tucked away and ready for the perfect moment. From the moment we landed in Florence, Nick was on the lookout. He’d done his research, but nothing felt quite right. Even his top pick—the stunning Basilica of Santa Maria Novella—was overrun with a pack of kids playing tag, which made for a cute but less-than-romantic scene. So, he waited. That evening, after the most delicious dinner and a quick gelato stop, we started walking back to our Airbnb. Olivia had just finished gushing about how incredible the Duomo was when we turned a corner—and there, seemingly out of nowhere, a cellist began to play the song 'A Thousand Years'. With the streets quiet and the moment unexpectedly perfect, Nick got down on one knee and asked Olivia to spend forever together. She said yes, and just like that, in the heart of Florence with a cello playing in the background, we were engaged. (No, the music wasn’t planned—but it couldn’t have been more perfect.) The next week and a half was spent drinking wine, eating cheese and being thankful for each other.