October 13, 2024, a date I thought was just our fourth anniversary. Troy and I had agreed marriage was still two years away, so a proposal was not on my radar. This was supposed to be a weekend of art, good food, and finally going on a trip that didn’t involve us hurtling down a snow-packed mountain. Also, this was New York—land of everything we love: art, theater, endless food, the energy of the city…and apparently, surprises.

Now, we’d decided to do one quintessential tourist activity on this trip that neither of us had experienced, so we picked the Empire State Building for some “classic NYC vibes” (the ultimate in corny romance, right?). Troy went all out, even arranging for sunset on the 86th floor, and told me to wear something nice because we were going straight to a romantic dinner. I, of course, was all-in for this plan, totally oblivious.

Flash forward to the morning of our anniversary, and I’m scrolling through old photos to make an Instagram reel of our greatest hits (which may or may not include us in ridiculous costumes). I was so emotional—like, full-on ugly-cry with tears emotional—reminiscing about our years together. Troy? He was cool as a cucumber. He knew what he had planned and was giving zero hints.

After four hours at MoMA, which made me fall for him even harder as he explained art like the absolute hottie art nerd he is, we went back to the hotel to get ready. We dressed up for our dinner-slash-sightseeing, and off we went to the Empire State Building.

Once we’re there, Troy pulls out VIP tickets (yes, red carpet, fast-track, the whole nine yards), and I’m loving this special treatment. We hit the 86th floor, where I’m busy offering to take photos for other people, blissfully unaware of what’s coming. Then Troy suggests we go to the 102nd floor—one last NYC view at sunset. This floor has glass walls from floor to ceiling, and it’s like we’re on top of the world.

We find the same family from downstairs and swap photo duties again. I take their photo, Troy gives his phone to the mom, and then, out of nowhere, Troy drops to one knee in front of me.

I’m so stunned I blurt out, “Is this really happening right now?” I focus hard so I don’t accidentally blackout, only hearing him and seeing him as he asks, “Will you marry me?” Everyone else in the room disappeared, even though they were there, watching us and clapping! I say “yes” (of course), and he stands me up, about to put the ring on my finger…but on the wrong one. Cue the giggles as we fumble for the right finger before I burst into tears and give him the biggest hug ever.

Then came the FaceTimes—my parents first, while we held it together (sort of), and then Troy suggests we grab a celebratory drink before dinner. I agree, thinking this will give me time to breathe. So off we go in a pedicab, a.k.a. bicycle tuk-tuk, with Frank Sinatra’s “New York, New York” playing us into the evening lights.

We arrive early at the restaurant and settle in for a drink, and out of nowhere, I hear a voice behind me say, “What a beautiful ring!” I turn around, and it’s my sister! Ashleigh had flown in with her husband, Royce, to surprise us with a huge “Mazel tov!” That was when I knew Troy had not only pulled off the proposal but also planned the biggest surprise of my life.

It was officially the best night ever. For four years, Troy has never managed to surprise me. But he doubled down that night and totally nailed it.

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