If you’ve already read the first part of our Q&A series, you know a little about how Steph and I began our story together. This time, it’s my turn to share my side—how we met, when I realized she was the one, and how I eventually managed to pull off a proposal in Positano (after not one, not two, but four failed plans).
How We Met
In 2015, I moved back to Miami after years away. At first, my days were filled with work, catching up with family, and reconnecting with old friends. But as I quickly discovered, a decade can change a lot. Almost everyone I knew had swapped happy hours in the city for life in the suburbs—spouses, kids, newborns. No one was driving 20 miles downtown just to grab a drink.
So, I turned to Bumble. My approach was straightforward: if you didn’t live within five miles of me, shop at the same Publix, or hang out at the same restaurants, we weren’t going to work out. Simple enough.
Then one morning, I woke up to a fuzzy photo surrounded by a green circle, with Bumble suggesting I “expand my horizons.” Reluctantly, I agreed, widening my search radius to 60 miles. That blurred little photo? It was Steph.
We started chatting, and about a week later, she messaged me saying she was in Miami for work and asked if I wanted to grab coffee. We met at Panther Coffee in Wynwood, planning on a quick 30-minute meet-up. Four hours later, we were still talking, and before we left, we already had a dinner date set for that Wednesday. The rest, as they say, was history.
The Moment I Knew
There wasn’t a single lightning-bolt moment where I thought, This is it. Instead, it was gradual—like a quiet shift I didn’t notice at first. One day, I realized I wasn’t thinking in terms of “I” anymore. Everything had become “we” and “us.” That’s when I knew I had found the person I wanted to spend forever with.
The Proposal That Almost Wasn’t
Fast forward to May 11, 2019—the day I finally proposed. But the story behind it was anything but smooth sailing.
I had always pictured proposing in Positano, so months before our trip, I began researching photographers who knew the city. After weeks of calls, emails, and location scouting, I landed on the perfect plan: an early morning cliffside proposal. The soft morning light would be ideal for photos, and the crowds would still be asleep.
But then came the first curveball: a forecast of thunderstorms on the chosen day. Our photographer suggested moving everything up by a day. No problem, right? Except then our flight through Chicago was delayed nearly eight hours, putting us at risk of missing the entire plan. Somehow, we made it to Italy late Friday night, exhausted but relieved.
Proposal Plan #1: Cliffside Sunrise
Scrapped because of storms.
Proposal Plan #2: Private Boat
Sounded romantic and perfect…until Steph got violently seasick during a complimentary Amalfi Coast boat tour that morning. I thought, If I put her on another boat today, she’s going to kill me. Plan two was dead in the water.
Proposal Plan #3: Another Boat at Sunset
Still not happening, unless I wanted to propose to an unconscious, nauseous fiancée.
Proposal Plan #4: The Hidden Beach
With everything falling apart, the photographer and I scrambled to come up with a new idea. She suggested a small private beach nearby. The plan was simple: she’d pose as a tourist, I’d ask her to take a quick photo of us, and when she handed the phone back, that would be my cue.
And this time—it worked. At sunset, on a tucked-away corner of Positano, I finally dropped to one knee. The photos captured everything: the joy, the surprise, and yes, the ring box upside down in my hand. (Minor details.)
Looking Back
Was it stressful? Absolutely. But in hindsight, all those mishaps made the proposal even more memorable. If everything had gone according to plan, we wouldn’t have this story to tell—the flight delays, the seasickness, the last-minute pivot to a secret beach. It wasn’t perfect, but it was perfectly ours.
And that’s really the essence of love and marriage: rolling with the unexpected, laughing through the chaos, and knowing that no matter what plan falls apart, you’ll always find your way together.
