08/26/2014 09:57 am ET Updated Dec 06, 2017

The Nine-Year Proposal

We've been a couple since we were kids.


Since high school, where we first connected through late-night AIM arguments about the musical merits of Taking Back Sunday and who wrote a better English essay about The House on Mango Street. On our first date we ate Quizno's subs, saw Cameron Crowe's Elizabethtown and kissed in the parking lot of the movie theater, on the trunk of my parent's Volkswagen. My first kiss, I gently mashed my lips into Stephanie's face. From that moment forward we were an item, and over the next nine years we'd traverse the country together: college in Portland, graduate school in Chicago, work in Cincinnati.

As we grew older, relatives peppered me with questions about when we'd finally full-on commit. The truth is, for a long time, I was in no hurry. We already shared an apartment, a dog, a bank account. How much different could marriage be? Maybe more important, because we had grown up as a couple, it took some time for us to find ourselves as full-fledged, mature individuals. We made sacrifices for each other: Me moving to a city not conducive to my career for her job. Her financially supporting me while I was unemployed, and emotionally supporting me through the accompanying depression. Somehow we weathered every storm and marched on, stronger for the struggle.

Not that I hadn't fantasized a million potential proposals along the way: From presenting a ring on a silver platter as we dined like royalty in San Diego last year, to kneeling in the sand of Chicago's North Shore where we lived like paupers during grad school. But before, the timing had never felt right.

Which is why, as we finally settled into our adult selves, I became frustrated with the taxonomy of our relationship. Unlike "wife" or "fiancé," to just call Stephanie my "girlfriend" ("of almost nine years," I'd always add as a subtitle) didn't convey the gravity that nearly a decade of trials and triumph deserved. I wanted it to be clear to the world what we meant to each other. That's how I knew I was ready.

Around last Christmas, a couple of close friends invited us to join them for a summer vacation in Hawaii. I knew far before any flight bookings or swimsuit purchases had taken place that this was my time to pop the proverbial question. Little did I realize, despite the nine-year build up, what an exercise in patience even just six more months would become, as I had far too much time to overthink how the deed would go down.

Nine years of engagement anticipation supplies a lot of accrued pressure. I'm not extravagant by nature -- jewelry from J. Crew is my go-to girlfriend birthday gift -- but with the prospect of a destination proposal, paired with the weight of our long-time courtship, I couldn't help but feel that this moment had to be spectacular.

Aware I would not be the first (or thousandth) to propose in Hawaii, I plundered travel blogs and Trip Advisor threads for ideas. One person recommended the beautiful vista at the top of a giant crater called Diamond Head, and linked to a YouTube video in which a sweat-saturated man (the hike to the top is almost a mile long, and nearly vertical much of the way) knelt before his girlfriend, the cellophane-clear Pacific Ocean stretched out behind them. She burst into happy tears, and it was certainly a sweet moment, but the perspiration streaming off their smiling faces, combined with the tourists milling in and out of the frame behind them, seemed to sap the scene of romance.

Another online comment recommended driving up to the northern coast for a picnic. "Bypass the busy beaches," it said, instead offering directions to a deserted strip of shore only accessible through a hole in a chain-link fence on the side of the highway. "And since no one maintains the trees on this hidden shoreline, watch out for falling coconuts!" As serene as the setting might be, "Bride-to-Be Bludgeoned by Rogue Coconut" was a headline I'd rather avoid. This idea, too, was shelved.

Privately, I met with our travel companions to see if they had any suggestions. Canoe ride to a private island? Nope, couldn't trust myself not to fumble the ring into the ocean. Helicopter ride? Absolutely not, even moderate turbulence has me squeezing Stephanie's knee like a stress ball. Ring of candles in the sand after dark? Too Wiccan. With no progress made, I resigned myself to fly into engagement unknown.

Spontaneity makes me uncomfortable: I'm the sort of person that scripts out a rant before calling customer service. Which explains the anxious bounce of my leg on all three legs of our flights en route to Hawaii. After 15 hours of travel we arrived in Honolulu, where our friends picked us up in a Mustang convertible. As we drove through the night toward the east side of the island, wind whipped Stephanie's hair across her face in the moonlight. I could hardly wait to ask her. Tomorrow would have to be The Day.

The next morning, dressed down and oiled up, we made a beeline for the beach and made like solar panels, absorbing UV rays and conserving energy so we could shake off jet lag. Stephanie read The Goldfinch while I pretended to doze, secretly scoping out the area. The resort was surrounded by a series of rocky lagoons, and through prescription sunglasses I could spot a footpath following the coastline off into the distance. I made a mental note and took a gulp of frozen Mai Tai. After an afternoon of oddly-shaped sunburns -- specifically, in thin strips just above my knee, where bunched swimsuit had exposed marshmallow-white thigh -- we retired back to the room to de-sand and shower.

The hotel hallway smelled like clean diapers, and as my nostrils drew in the pungent promise of future baby an idea came to me. I turned to my three companions and said, "Let's go for a walk at sunset."

Our friends are expecting a baby in November, so as Stephanie cleaned up, I told them this might be an ideal time for "unexpected pregnancy pains" to prevent them from joining our sunset stroll. I retrieved the ring. An attempt to stuff the entire velvet box into my pocket produced an awkward lump, so I decided to ditch the vessel and let it ride solo. Stephanie emerged from the bathroom, and after some minor cajoling -- "I don't want to leave them if Emily's not feeling well!" -- we hustled out to the beachfront just as the sun began its initial descent.

I had no clue where the path would take us, and as we wove our way off of the resort grounds I grew nervous. Though the water reflected a beautiful palette of pink, yellow and orange, the surrounding sand was filled with noisy families. A dad digging a hole, children eating Pringles, a teenager playing Pitbull on an iPod speaker. Not that I could begrudge them for enjoying their vacation, but as for a proposal location, while the setting itself was right the staging was all wrong.

Soon we reached the end of the paved path. From there, a dirt trail jutted off into a lava-rock peninsula, where wind was toying with a fisherman's line. I grabbed Stephanie's hand and we made our way to the outermost point. About halfway there, I saw that by some cosmic coincidence, the Beatles' lyric "Love Is All You Need" was spelled out in white pebbles on the ground. At the end of the rocks we were close enough to the sloshing waves that they wept droplets onto our legs. I had goosebumps; from the ocean spray or nerves, I couldn't say.

"You know," I said, "I love you."

"I love you too," she said.

The sun fell below the horizon. I fell to one knee.

"Will you marry me?"

I trembled on the words, and almost had to spit them out. So much time had been spent examining this moment clinically that I hadn't realized how emotional I'd be.

"Yes," she said, then started to cry.

We embraced and held it, the summation of a decade posed in tableau, then headed back to the hotel.

I can now say with confidence, drawn from personal experience, that performing the perfect proposal doesn't necessarily mean engineering the most elaborate, precisely plotted scheme you can imagine. No flash mob of dancing friends or carefully crafted video is needed. It's the act itself that's important. I could've proposed at dinner or on a hike, in a house or with a mouse -- it would've been special no matter what.

We've come a long way since those teenagers kissing on a car trunk, but in some ways we haven't changed at all -- except now she's my fiancé, not just my girlfriend (of nine years).