The One Where We Got Engaged

07 10 2020 | NAPA, CA

He asked if I knew and to be honest...I did. I didn’t know when and I didn’t know where and I didn’t know how. But I knew. I knew because he would look at me and tell me he couldn’t wait for me to be his wife. Knew because we’d dreamed about the day, browsed rings together on many occasions and talked about it often. I knew because of the sadness in his eyes, in my eyes, the moment we realized we’d need to officially postpone our trip to Mexico in March of 2020. The trip.

An unspoken heartbreak because we both—knew—but would and could never fully say.

But I knew.

I knew because my parents would have been on that Mexico trip with us. I knew because his own parents also mentioned wanting to come for part of our trip. And I knew because one night, after a martini (or two), he told me. Tears in his eyes, he spoke about the day he planned in Mexico for us: the photographer he hired, the sweet little room at a hotel he found, the months of coordinating…the trip we had to cancel.

So, yes, to an extent, I knew.

I knew an engagement was coming, yet the details—the day, the plan, the weekend—I could have never fully known the moments of joy it would bring for us.

Several months later, we planned a summer trip to Napa. Our first social-distanced mini getaway in one of our favorite places. A trip we honestly also postponed multiple times. But there we finally were. Happy and together.

We started the weekend early, checking in on a Thursday, eager to have a weekend of relaxation. That first night we spent some time scouting a picnic spot. The idea wasn’t anything out of the ordinary, really. Something I’d been dreaming up for months. “Let’s pack a picnic and enjoy it in the park.” So it was quickly decided: our Napa trip would include a picnic.

“We can have it Friday evening at Golden hour and take a few photos,” he said. A usual occurrence, really. Location scouting + waiting for golden hour.

The Mansion Garden at Silverado was the spot. We celebrated my 30th at the resort and fell in love with its idyllic and intimate vignettes. To us, The Mansion Garden feels like it’s somehow just our own.

The next day—the day—we spent a leisurely morning ordering room service; eating bagels & lox and black coffee on the patio. Sunshine streaming on our faces, pure bliss. Post-breakfast and with swimsuits packed, we headed to the pool. Lunch, lounging and several hours later, we headed back to the room to change and get ready for dinner. But first, our picnic.

The picnic.

Friday evening, as golden hour approached, we packed our picnic basket with champagne and charcuterie. The picnic blanket he gifted me for my birthday a month earlier.

We strolled over to the garden and he set the whole thing up, perfectly placing the blanket and topping a plate with all our favorites.

We sat and sipped, soaking up our first moments of relaxation after several months of being home. The whole lawn and garden to ourselves. Later, he prompted me to take a few outfit photos. The photos weren’t anything out of the ordinary, him orchestrating the mini photo session, however, was a bit new. As he directs me, he suggests turning around for a few photos. My mind piques.

In this moment, I know my mind is running through the list quickly: did he have a ring in his pocket? Surely I would have noticed.

And then, suddenly, he calls my name.

“Tyler…

….you’re my best friend”

…

“Will you marry me?”

A blur. Our photographer pops out from behind a building. He slips the ring on my finger, pure joy on his face. Absolute elation in the moments that ensue.

They walked me through the details, how he texted Jessica a photo of our location (the one he snapped the night before), how they planned the timing, how she had been waiting in anticipation behind the building for the exact right moment.

We’re elated and giggly and I’m soaking it all in. We’re soaking it all in.

Staff is appearing now as if out of nowhere. More champagne glasses, sweet words and congratulatory toasts. We’re on top of the world.

We continued the evening with a surprise engagement session, FaceTimes, texts and calls to our loved ones. Dinner at the resort. Many more sweet wishes. Surprise bottles of champagne from the resort & from friends. (The sweetest). Chocolate-covered strawberries. Carrot cake. Pure joy.

It was the perfect evening, the perfect weekend and one of the happiest moments of our lives.

I can’t wait to marry this one…

Photos by Jessica Kay