If you’ve been following along, you may have already read the first part of our Q&A where I shared how we met, our engagement, and my own thoughts on marriage. But this time, it’s my fiancé’s turn to tell his side of the story—and trust me, you’ll want to hear it. From the swipe that changed everything to a proposal that nearly unraveled three times, here’s how it all unfolded.
How We Met
In 2015, he moved back to Miami after being away for years. Those first six months were a blur of work, reconnecting with family, and catching up with old friends. But in that time, he realized just how much life had shifted—nearly everyone he knew was now married, with kids, living far outside the city. The reality was clear: spontaneous happy hours weren’t happening anymore.
So, he turned to Bumble. His logic? If someone wasn’t living within a five-mile radius, shopping at the same Publix, or dining at the same local spots, they probably weren’t the one. Simple and efficient.
Then one morning, a fuzzy photo appeared on his screen with a green circle around it. The app suggested he expand his search radius. With one click, his world opened up from 5 miles to 60. And there I was—Steph.
We chatted for about a week before I messaged him to say I was in Miami for work. Coffee at Panther Coffee in Wynwood seemed like a safe, short first meeting. But what was supposed to be 30 minutes turned into four hours, ending with plans for dinner that same week. And the rest? Well, you could say it was history in the making.
When He Knew
There wasn’t one grand, cinematic moment when he realized he wanted to spend forever with me. Instead, it was a gradual shift—subtle but profound. One day, he noticed he no longer thought in terms of “I” or “me.” It had become “we” and “us.” That small but powerful change made everything clear.
The Proposal That Almost Wasn’t
Deciding to propose in Positano felt like a dream. He wanted the moment captured, not for himself but because he knew how much it would mean to me. Months before our trip, he spent hours combing through photographers’ portfolios, chatting with them about lighting, angles, and logistics. Eventually, he settled on an early morning cliffside proposal—soft light, fewer tourists, a picture-perfect backdrop. Everything was meticulously planned for Sunday morning.
But travel has a way of laughing at our best-laid plans.
First came the weather forecast: 80% chance of thunderstorms on Sunday. The photographer suggested moving the proposal to Saturday. Fine, problem solved. Except then our flight from Chicago was delayed eight hours, threatening to derail everything. At one point, it wasn’t even clear if they’d let the plane leave that night. He panicked, emailing the photographer about backup plans.
Enter Plan B: a private boat proposal. He’d rent one boat for us, the photographer would rent another, and together they’d capture the moment against the sweeping Positano skyline. Romantic, yes, but also rushed—just two hours after landing in Italy.
By some miracle, the flight wasn’t canceled, and we arrived Friday. The next morning, nerves creeping in, he had a drink (or two) at breakfast before asking the concierge for activity recommendations. The suggestion? A complimentary boat tour of the Amalfi Coast. Perfect… until I got seasick ten minutes in. Let’s just say, the idea of putting me back on a boat later that evening was officially out of the question.
On to Plan C.
Defeated but determined, he emailed the photographer again. She came back with a solution: a secluded beach nearby, perfect for a quick, intimate proposal. The plan was simple—meet her on the beach, ask her to take a selfie of us, and when she handed the phone back, he’d drop to one knee. She’d capture the moment before anyone could shoo us away.
And so, with Plan D in motion, he finally pulled it off. The proposal was everything I could’ve dreamed of—romantic, surprising, and perfectly imperfect. Sure, the ring box was upside down, but by then none of that mattered. What mattered was us.
Looking Back
When I ask him now what he remembers most, it’s not the stress of the flight delays or the panic of scrapped plans. It’s the quiet certainty that no matter what went wrong, the one thing that mattered went right.
Because in the end, proposals aren’t really about flawless execution or cinematic perfection. They’re about two people choosing each other, again and again, even when the plans fall apart.
And that’s exactly what happened in Positano.
