As I shut off the engine and stepped out of our rental car, I took a moment to breathe. I felt the light Atlantic sea breeze on my skin and tasted its salty essence on my tongue. The Portland Head Light towered in front of me on a day too warm and sunny to be a Sunday in the middle of November. I heard the laughter and excitement of friends and families soaking in the final serene afternoon before the coming harsh Maine winter.
I grabbed my backpack from the back seat, an action you found suspicious. You likely thought the following: Why do I need my backpack if we are just observing the cliffs and taking Christmas card photos? Do I have an ulterior motive? Am I storing an item inside, such as a ring? I brushed away your suspicions, all of which were correct, and we began our trek.
At the time, you were unaware of Janelle, our photographer who was waiting by a previously agreed upon location overlooking the cliffs and lighthouse. As we made our way toward her, we journeyed down that steep dirt path. You know the one. When we attempted that hill earlier in the year, I struggled, requiring a great deal of assistance from you. This time, I descended confidently down the hill, perhaps too confidently, as you lagged cautiously behind. My increased strength and newfound confidence were the result of our exploring the city each weekend since we had last visited the Head Light. This served as a microcosm of a larger theme of our relationship, whereby you have pushed me to be open minded and tear down self-imposed barriers.
When we passed Janelle, I secretly gave her a nod, acknowledging that our plan was in action. You had a mind of your own, of course, and found an outlook up a trail to take photos. I had no choice but to follow you. As we posed before your camera, I noticed the park was busier than I had anticipated. I messaged Janelle that I might be calling an audible.
As we wrapped up photos, I claimed I was fatigued and needed a sitting break. You pointed to a bench along the main walking trail overlooking the water, which was the original location of my big surprise. However, I felt the spot was too busy for such an intimate moment. I fought your suggestion and told you to follow me farther up the hill.
That’s how we ended up in the brush—an overlook filled with sticks and barren vegetation. We found a red picnic table to sit as Janelle slowly crept up the hill behind us. By this time, you were completely aware of my ulterior motives. You said, and I quote, “Babe, I’m scared. Can we please go back to the car?” I replied that we could not and asked if I could read you a note I had written earlier that day. I’m not sure if I fully processed reading that note aloud or if you even comprehended it, as we both knew what was coming. As I concluded my note, I reached into my backpack, confirming your suspicions. I pulled out a Tiffany blue box and said, “Well, I should probably do this right,” as I got down on two, not one, knees. I then asked if you would marry me, and you said yes.
Our proposal came together quite quickly—the logistics of finding your ring, deciding how I would propose, and actually proposing occurred in a little over a month. This does not mean I cut corners; I just innately knew what needed to be done. Perhaps, the ideas had been ruminating subconsciously for years.
Let’s begin with the story of choosing your ring before detailing how I decided to propose.
The Ring
For the past year, we had tossed around the idea of your trying on engagement rings. When we returned from your dad’s retirement ceremony and vacation in early October, I decided the time was right. I booked us an appointment at Tiffany’s flagship store, The Landmark, as I wanted you to try an array of rings in an iconic setting. You had shown me TikToks of Tiffany beforehand and shared how many couples stop by Tiffany when looking at rings for the classy, unique experience.
Unfortunately, our experience was poor, as the lady assisting us likely caricatured us as young tourists wasting her time. However, we were serious with our intentions. Regardless, we tried on numerous rings, and you were fond of the elongated and exquisite emerald and oval shapes.
After leaving The Landmark and reflecting on what ring I wanted to give you, I knew the ring had to come from Tiffany, even though we had a subpar experience with the lady. Initially, I was conflicted with buying a ring at Tiffany over a local jeweler, as you know how much I prioritize local businesses in other aspects of my life—not due to a false sense of altruism but due instead to generally receiving better value. However, I could not bear giving you anything less than what I deemed the best, as the ring symbolizes my commitment to you and our future union. To me, Tiffany’s legacy and craftsmanship were superior, so that’s how you ended up with a blue box.
About a week after we visited The Landmark, I scheduled an appointment at Tiffany in Hudson Yards. While I knew its selection would be smaller, I didn’t want to return to The Landmark. I also appreciated that we have happy memories at Hudson Yards. I wore my best outfit, even donning my Italian leather sneakers and shaving my face (a rarity), as I hoped the staff would take me seriously. I did not want a repeat of our first experience.
I met with Justina, and I felt more seen and respected. I always connect well with millennials. I told her I was looking for an emerald or oval shape on a pavé platinum band. A platinum band was imperative since I knew you would never take it off, so it needed to be durable. As expected, she didn’t have much in house to show me. However, she was going to research rings in my budget and bring them into the store for our next visit.
The following week, I stopped by to see the emerald and oval rings she had sourced. You and I had had a conversation that weekend where you reiterated your desire for an emerald, mostly because of its elegant nature and partly because your grandma has one. This information biased me toward the emerald; I eliminated the oval. I was not yet ready to move forward with the emerald she had sourced just yet, though. I asked Justina if she could bring in similar rings.
I awoke the next morning knowing I was going to buy the emerald ring I saw the previous night. I am not sure why or how, but I allowed my feelings to guide my course. I messaged Justina and asked if we could meet again that night; I expressed I wanted to move forward with the emerald she had found.
When I arrived at the store that evening, Justina sat me down and grabbed the Tiffany blue box. I had a feeling she was going to pull out all of the stops to make this sale, and she did not disappoint. When I opened the box, the ring was so pristine and sparkly—even for an emerald. I felt in that moment I would give you that ring.
I sat with the ring for a few minutes. Justina brought me champagne. I began waxing poetically, as I do whenever I drink, about the meaning of this ring and its symbolism. Justina was a great sport and allowed me to express my thoughts.
We then moved to the climax—purchasing the ring. I naively asked if there was any room for price negotiation. As expected, there was none. To be fair, I had no leverage, and Justina knew that. I pulled out my AMEX and prayed the purchase wouldn’t be declined. It wasn’t. I was the new owner of a Tiffany engagement ring.
Justina sent the ring for cleaning and resizing. I would pick it up the following week. By that point, I had decided how I was going to propose to you.
The Proposal Plan
Buying the ring, while financially and symbolically challenging, was easier than designing the proposal plan. How could I propose to you in the most meaningful way possible?
I began with the geographic location—where should I propose? While the city is meaningful to us, I didn’t feel we have strong enough roots here yet. NoVA was off limits. Baltimore felt like taking a step back. Vermont is special to you but not us collectively.
Maine is the only place that feels wholly ours. Yes, you visited when you were younger, but many years have passed. We journeyed to Maine earlier in the year and had the most wonderful time; we love our lard donuts, local boutiques, and fresh food accented by a coastal aesthetic.
If I was proposing in Maine, the Portland Head Light was the spot. The park is straight out of a novel with its jagged cliffs etched over a millennia by the Atlantic. What a powerful place to signal our commitment that will last until our last breath.
And, as you had expressed for years, we needed someone to capture that commitment. Enter Janelle. I was drawn to her warmth and expertise during our initial call, as she played the combined roles of photographer, event planner, and therapist for me. Planning a proposal is difficult! Janelle recommended the Head Light or a beach farther down the way. While the beach was pretty (and definitely more picturesque than my brush), I had my sights set on the Head Light. We agreed on the time and place of the proposal—the 17th at 2:30p on a bench overlooking the water and lighthouse.
You were skeptical of my incessant desire to take a trip to Maine, especially after I had shot down a weekend in the Hamptons as we needed to “save money.” However, I bluffed and convinced you I needed the trip to recover from work burnout. (I would’ve been a phenomenal actor.) We soon after booked two nights at Docent’s Collection in Old Port and rented a car. My plan was in motion.
Lastly, I needed a restaurant to celebrate our momentous occasion. I found Twelve, a spot founded by a NYC chef that sources high-quality local ingredients to craft dishes paying homage to Maine. That was good enough for me. I had also never found a restaurant with such strong reviews.
Picking up the Ring
The ring was ready to be picked up a few days before the proposal. I scheduled an appointment at 5:30p on Thursday to grab it.
My work was hectic that day. The business was concerned about one of its trades, which required me to dig into confirms to ensure the booking was accurate. 5:30p wasn’t going to work; I messaged Justina that I would be late.
I arrived at Tiffany around 6:00p stressed and anxious. I knew I needed to log back on to work and assist with any outstanding issues. At the same time, I had asked your parents earlier that day if I could call them at 7:00p regarding a surprise I was planning for you.
Justina picked up on my stress and asked if I wanted a champagne. After all, this was a very important milestone. I asked for the champagne, downed a fair bit of it, and settled in to the appointment.
She brought over the ring in its Tiffany blue box. As I unlatched the box, I was awestruck by the ring. It was fantastic. For a brief moment, I allowed myself to feel proud that I could pull this off. My work ethic and saving the excesses of my labor over the past years permitted me to buy this ring.
While I finished my champagne, I filled Justina in on my proposal plan, which would be executed in fewer than 72 hours. She was elated. We decided then that after the proposal I would bring you in to meet her, establish a connection, and check the ring on your finger. I had hoped that through introducing you to Justina that you would understand why I stuck with Tiffany even after our subpar initial experience.
Before leaving, I hid the ring in the bottom of a take-out bag that Dan gave me at work that day. Originally, I had planned to grab my backpack from home before the appointment, but I had run out of time. Thus, I left Hudson Yards with the most expensive item I own in a take-out bag in my scooter basket.
I arrived home with heavy legs and a relaxed attitude. I confidently dialed your mom’s number. We greeted each other, and she shared how she and your dad were finishing packing for their Antarctica trip. I then let them know that we were going to Maine and that while you believed the trip was for resting and relaxing, I was going to propose. Your parents were very excited and shared some kind words, most of which I cannot remember due to the stress of the event. I told them we would find a way to call them after the proposal, even though they’d be at the bottom of the world.
Being on an adrenaline high, I then logged back on to work and sent the most banger of an email I’ve ever sent recapping an issue and detailing next steps.
Proposal Day
The 17th began with an early alarm. I needed space to reflect upon on the coming proposal and what it meant for our lives.
I sat in the rocking chair in the living room and opened the Notes app. I jotted down a “proposal speech” that I wanted to share prior to getting down on one knee. I knew myself well enough to know that if I didn’t have a note I would likely freeze or crack or not say what I wanted. As I finished my note, you awoke, and we started our morning.
We first stopped at HiFi Donuts to munch on lard donuts and sip our espressos. Cheers to seed oil-free donuts! I was distracted listening to a bitcoiner (not be confused with a crypto bro) trying to orange pill his friend. He was doing quite well. I digress.
We then mosied on over to a block of Portland boutiques. We were priced out of many of the stores selling high-end designer clothes. However, we found a Maine gift store and a pet store for Nado.
The Maine gift store (Lisa-Marie’s Made in Maine) is quite special to us looking back. We bought a couple items, such as a picture frame of a couple snuggling on a cliff made out of rocks and a Maine ornament, that mean a lot to us now given the significance of the day.
Around noon, I started to get antsy (typical), as I knew we needed to eat lunch and stop by the hotel before heading to the Head Light. I had to move you along without your being tipped off. We stopped by Eventide to put our name on the list for lunch and then headed down the street to our hotel.
Back in the room, I had to subtly and seemingly nonchalantly persuade you to change into an outfit you’d deem “proposal worthy.” Luckily, I succeeded, as you said something like, “Babe, you could propose to me in this outfit.”
As we walked back to Eventide, you bolstered my confidence by saying, “You are acting too calm to propose to me today.” I thought I might just pull this off.
For lunch, we had lobster rolls, which were good but nothing to write home about. The food came faster than I expected, so I had to stall to prevent us from arriving at the Head Light too early. I ate slowly, and when it was time to drive to the park, I took the long way.
—
After the proposal, which you read about above, we took photos with Janelle for thirty minutes. This was a fantastic idea, as some of these pictures will live on for years to come.
We then headed back to Old Port to grab a seat at the Cellardoor. Over wine flights, cheese, and crackers, I debriefed how the proposal came together. You enjoyed the play by play. Looking back, I’m glad we took time to do this, as it made the engagement even more meaningful.
We ended the night with the best dining experience either of us had ever had. As we worked through our multi-course dinner, we basked in the emotions of being newly engaged.
Final Thoughts
While you know this story, my perspective of our engagement will now live in perpetuity on my website. You can visit and re-read it whenever you’d like from wherever you are. Further, I hope others with an intention of proposing will read about our story and view my efforts as an example, as you were quite impressed with my work (not an easy feat).
I love you, Caroline. I am honored and lucky to be engaged to you. I am excited to continue planning our wedding and ultimately tie the knot.
—KH