By: Preston Young
On Friday, April 25th, I got engaged to my girlfriend (now fiancée!), Rachel! And because it was all very real, very exciting, and very nerve-wracking, I figured I’d answer the questions everyone’s probably wondering—When? Where? How? Did it go smoothly? Did Mason play a role? Let’s back it up.
For weeks leading up to the proposal, I was coordinating with a photographer from Long Island who, bless her, walked me through everything. I’m talking positioning, wind direction (very important for Rachels hair, apparently), the exact degree to stand at, how long to stay on one knee, you name it. I learned more about proposal staging than I ever thought possible.
The original plan was to pop the question on Saturday. But about a week out, the weather forecast looked quite dreary, so I made a game-time decision and moved everything to Friday. Easily one of the best calls I’ve ever made, especially given the day and night we had on Friday.
We kicked off the weekend with a ferry ride from Bridgeport to Port Jefferson, made our way through the Hamptons, shopped, stopped for lunch, wandered around, and eventually checked in at the Montauk Yacht Club, way at the end of Long Island. After a walk around the hotel and a drink at the bar, we headed upstairs to get ready.
Now, getting ready was a whole event on its own. Even though we’d planned our outfits before we left, I still had to make sure everything coordinated perfectly, a non-negotiable for Rachel, especially when it comes to photos. I also had to make sure her nails were done beforehand, so there was a subtle mental fist pump when she got them done while still at home on Thursday. Then came the ring. I had to sneak it in my luggage on the way there, then into my pocket without her noticing, hoping she wouldn’t catch me doing a weird pocket shuffle. And getting it out from its hiding spot without her seeing? That was a whole other level of panic, especially as we were getting ready. So, I’m juggling all of that, holding onto the ring, making sure she doesn’t suspect a thing, following the photographer’s checklist over and over in my head, and trying not to combust from nerves. No pressure!
I don’t get anxious often. I can handle back-to-back meetings, last-minute plan changes, and even those moments when a client calls, and I know something big is about to come up. But that Friday? I couldn’t eat. Barely slept the night before. Just pure, proposal-induced adrenaline. I had picked up the ring the day before, and it was very real. It was happening. Tomorrow became today, quickly!
We drove out to the Montauk Lighthouse about an hour and a half before sunset. Below the lighthouse, on a quiet little beach, I asked Rachel to marry me. I don’t remember exactly what I said—it started strong, I think… but somewhere between pulling out the ring and getting down on one knee, time kind of blurred. All I really know is that she said yes, and that’s what matters.
Our photographer captured the whole thing, and afterward, we spent about an hour and a half taking engagement photos. Rachel didn’t want anyone to know ahead of time, so getting to FaceTime everyone after and share the moment live was incredible.
Back at the hotel, the room was decorated with flowers, champagne, and a gift from Mason – a ring-shaped dog toy and an ornament.
After photos and calls, we went to dinner at Topping Rose House, a Jean-Georges restaurant in Bridgehampton. The food was incredible, but honestly, I don’t remember much of the meal, I think the nerves were still hanging on. I kept looking across the table thinking, “Whoa. We’re engaged”.
The next day we grabbed breakfast, drove around the Hamptons looking at mansions, did some shopping, and spent the rest of the day enjoying life as fiancés. No big plans. Just soaking it all in.
Looking back, I wouldn’t change a thing. The planning, the nerves, the secret-keeping, the wind checks, the dinner, the champagne—all of it was perfect.
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