Planning to Propose

A story for family, friends, and our future selves.

3,531 words

Elizabeth and I first talked about marriage almost two years ago, while admiring the Manhattan skyline at a wedding after party. As our relationship deepened, our conversations slowly transitioned from discussions of what we each wanted to discussions of what we both wanted. Eventually we were making plans to visit wedding venues, thinking about possible dates, and sharing a Google Doc with a guest list… but we were not yet engaged.

I wanted to propose, and Elizabeth wanted me to propose. Although the question itself was expected, I still thought she should feel surprised. This was also something I would get to do only once, so I wanted the moment to be personally meaningful, intimate, and romantic. We had plans for the third anniversary of our first date in mid-December, but that was a too-obvious time to pop the question. What could I do instead?

I drafted the below story, then asked Elizabeth to make the block-quoted sections her own, adding and removing details as she saw fit. My thoughts and behind-the-scenes commentary are between the block quotes.

Last year for Thanksgiving I spent a wonderful holiday with Steven and his mother’s family outside of Buffalo, NY, so this year Steven wanted to return the gesture by coming home with me to Tacoma, WA. When buying our plane tickets, I ultimately wanted to be home for longer than Steven felt he could be away from work, so he planned to fly out after me and leave earlier, arriving the night before Thanksgiving and departing the following Monday night. I, on the other hand, would be leaving Seattle the Wednesday after Thanksgiving for San Francisco, where I would have the first of three internship/residency interviews in three days (all in different states and straddling both coasts).

So Tuesday, December 3rd was the day that I was planning to propose.

In an earlier version of the plan, before she had those interviews scheduled, I was going to surprise her at the Seattle-Tacoma airport before her flight home from there to NYC. I’d book us both tickets on a flight later the same evening, and make a reservation at a fancy restaurant near the airport to celebrate.

While airports are perhaps not the most romantic of places, SeaTac has special meaning for us. First, Elizabeth received my initial OkCupid message when she was at that airport. Second, when I went to visit Elizabeth in Seattle in the August of 2011, we both thought our return flight was three hours later than it actually was. We realized this mostly too late, but still rushed to the airport. They were closing the boarding doors just as we were arriving at the gate, but they had given away one of our two seats to a standby passenger. We would have made it sooner, but Elizabeth’s stethoscope held her up in the security line! Rather than split up, we decided to stay together. We got to have another lunch with her brother, and then spent a long day at the airport, and had an arduous four-flight journey back to NYC… but we were in good company, so it wasn’t so bad, and the mild adversity brought us closer together.

While Steven was boarding his flight from JFK to SeaTac, he texted to let me know that he had gate-checked his carry-on and it might take him a few extra minutes to get to the curb outside of baggage claim.

If I was going to surprise her, then it seemed even better to surprise her wearing a suit. So in my carry-on I packed a garment bag and some hangers along with my suit, tie, pocket square, belt, socks, and dress shoes. It would have been difficult to take the suit to Elizabeth’s house — if she had seen it, how would I explain having brought it? — so instead I left it at luggage storage at the airport. I wasn’t checking a suitcase, and the suit and shoes are bulky, so this required under-packing for the rest of the trip, which in turn meant I had to do laundry and claim I miscounted the number of days of clothing I thought I’d need. I knew it would take some extra time to extract these things from my carry-on, transfer them to the garment bag, and find the luggage storage desk, so I made up the story about gate-checking to buy time.

Later, while unpacking and repacking for our weekend trip to Port Townsend that weekend, Elizabeth had a few occasions to see what I had brought with me, so while I could have hidden my suit in a closet at her house, it would have been risky. Maybe I could have dispensed with suit entirely, but I think it added a lot to the surprise, and she appreciated that my tie matched her sapphire.

Steven’s flight was without incident, but I was having adventures of my own while navigating holiday traffic to reach the arrival terminals. Once Steven got in the car I tried not to sulk about my tiff with the airport traffic cop, but it still probably wasn’t the jovial welcome he had expected. On the half-hour drive from SeaTac to Tacoma, I commented about the weather forecast, which was predicting snow on the evening of his departure a few days later. “Perhaps you’ll get stuck, and have to stay longer after all,” I said hopefully.

But this was exactly what I was planning to do! I had booked a hotel near the airport for the Monday night I was supposedly taking a redeye back to JFK, and was planning to stay there, propose on Tuesday, and fly with her to SFO on Wednesday.

I also asked how he had spent the first part of his day, and he mumbled something about “I don’t remember, just email and reading.” Now, Steven rarely forgets what he does with his day, but it was late and he’d had a long flight, so I didn’t think too much of this lapse in memory.

This was because I had spent the day running frantically around Manhattan looking at engagement rings, and hadn’t thought to come up with a better alibi. I had done a ton of research online beforehand, so I planned out a route and tried to see as many rings as I could before my flight. I knew she wanted a sapphire, but after going to several shops, I decided that what I really wanted to do was pick out a gemstone and a setting with her rather than try to find something I liked that I was also confident she would like. I ended up getting an inexpensive ring with which I could propose, and intended for us to later pick a nicer ring out together and keep the other for sentimental reasons.

Steven, my mother Angela, my brother Andrew, and I were going to Port Townsend for two nights the Friday after Thanksgiving. My dad passed away several years ago, but Steven still wanted to ask my mom for my hand in marriage, and I agreed that she would appreciate the gesture. He’d been hoping for a quiet moment alone with her for several months, but there hadn’t been any good opportunities, and a phone call didn’t allow for the desired sincerity. Finally, on Saturday in Port Townsend, I left with my brother to park the car, leaving Steven alone with my mom. I knew what he was up to, which made it a bit awkward as my brother and I repeatedly drove past them in search of a parking space. When I returned, however, they were both all smiles.

In retrospect, this went much more smoothly than it could have, but I was too busy worrying about the proposal plan to psych myself out.

This is when I first told Angela about my secret alternate travel arrangements, and it was just in the nick of time, since I’d have wanted to cancel the hotel reservation near the airport if the whole plan was to be scrapped. Angela was happy to help get Elizabeth to a particular place at a particular time on Tuesday, since she was taking the day off from work anyway. We agreed to both brainstorm a bit and figure out the details later. I had originally been reluctant to tell Angela or Andrew about the plan, since I know that I was acting weirdly, and I felt like the more people that knew, the more likely it was that Elizabeth would grow suspicious. But in retrospect, I needn’t have worried, and they were both great.

Over the next couple of days Angela and I had a few secret conversations about where a good place would be to propose. We talked about the ice skating rink in Tacoma, the Chihuly Bridge of Glass, the ferris wheel in Seattle, and the Space Needle, but I kept coming back to REX/OMA’s Seattle Central Library. I once got to see the architect, Joshua Prince-Ramus, speak at Stanford about the project, and it even has a TED talk! There was something about my favorite place in her favorite place — the building within her home city/state — that just felt right.

We travelled back to my home outside of Tacoma on Sunday, and on Monday Steven and I spent the day together. I showed him some more of the parklands in Tacoma, and we had a nice, simple lunch. We talked a bit about engagement rings, and he shared the research he’d done as we reviewed his related Pinterest board. I imagine buying an engagement ring alone is much like selecting a very expensive tattoo for someone else, so I was happy with the idea of picking something out together. Despite all this talk, a proposal still felt remote. We didn’t even have a ring, right? Still, Steven is a master planner of surprises. He is the most detail-oriented person I know, and whatever he might say to suggest the proposal was far off, I knew that it would be a complete surprise.

It was a little weird to be having this conversation while I had the ring in my pocket! Also, the Five Mile Drive is beautiful, and at one moment it was tempting to get down on one knee there, but I kept my resolve and waited.

After lunch we drove up to Seattle. One of Steven’s favorite buildings is in the city, . Steven and I had explored the building together on his first trip to visit me in Washington two years before, and he said that he’d like to visit it again on our way to dinner.

After a little difficulty navigating through Seattle and finding parking, we enjoyed wandering through a building flooded with light from the setting Sun. As soon as we got outside, Steven made an abrupt comment about needing to make a quick phone call to a friend. He said that he’d been trying to touch-base with this person for days, and asked if we could go back inside the library where it was warm (Seattle temperatures have been unusually low this winter). Despite the simple request, I was reluctant. The day was waning and I was hoping to enjoy the relatively new ferris wheel on the pier during sunset. Steven was insistent, though, so we gave up on that plan and I read the news on a computer in the library while he went off to make the call.

I actually called Angela from the library instead of my friend, and we talked about more details for the next day. I needed to go back inside to make the call so that I would have a few moments out of Elizabeth’s line of sight during which I could plausibly have taken out my notebook. I was not at all smooth about doing it though, and nearly ruined the whole plan. Fortunately she was only frustrated about the missed sunset, and not otherwise suspicious.

It was a surprisingly short call, and afterward we continued on down to the piers and to one of our favorite bars. We went from there to dinner in Ballard. Finally, I drove Steven to SeaTac for his redeye flight back to New York, and we said goodbye.

An hour or so later, he called me in a panic — he didn’t have his notebook! He told me that he had last seen it at the library, when he took it out to jot something down while he had been on the phone, and that he would call them in the morning to see if they had it. I know how important Steven’s notebook is to him, and I felt terrible that he had forgotten it, which I can only recall him doing one other time in the past three years.

After Elizabeth drove away from the airport, I pretended to check in for my flight and walk toward security, and then called her mother again to finalize more of the details for the next day. After that I left the airport and walked (in a light drizzle… maybe I should have waited for the shuttle?) to the aforementioned nearby hotel. I got my room key, dropped off my bag in my room, and called Elizabeth from the hotel lobby, hoping that the background noise would sound similar to that in an airport. I actually cut the timing pretty close and nearly waited to call until after my flight was supposed to have taken off, but it was fine. Of course I still had my notebook safely in my luggage — I had considered actually leaving it at the library, but it seemed too risky given how uncertain the whole thing was.

Since my mom would be taking the day off, we planned to spend time together. I didn’t know, however, how interested she was in going into the city. Having just been there, I was a little exhausted by the idea of driving back up again the following day. I suggested to Steven that he simply have the notebook mailed, but he was so reluctant that I felt bad for suggesting it. Maybe he was worried it would get lost in the mail? What’s in that notebook, anyway? I told him that my mom hadn’t mentioned anything about going into the city, so he said he’d get back to me after the library opened at 10am and he had confirmed it was even there. Just before I headed off to bed, my mom seemed to have a revelation about what she wanted to do tomorrow: “Oh, let’s go to Seattle! I haven’t been in so long. Maybe we’ll try the Cinerama!” Her sudden enthusiasm was impossible to refuse and we started to excitedly plan our day.

The next morning Steven texted to say that the library did have the notebook, but that it wasn’t at the regular Lost & Found, but rather at the Special Collections desk in the Seattle Room on the tenth floor. I let him know my mom and I were in fact coming to the city, and we would stop by to pick up the notebook.

By this point, I was already back at the library! I had woken up early, put on my suit, and taken a cab back to Seattle, so it was a sigh of relief to hear that they were, in fact, coming to the city. If Elizabeth hadn’t been up for it, I would have had to get myself to Tacoma (40 miles away!) and find some other way to surprise her. My worst case backup plan was to wait until she left the house to take their dog Jack for a walk… but it was cold outside, and that wouldn’t have been nearly as romantic.

The library’s Lost & Found is at the security desk on the ground floor. It’s busy and not especially pretty down there, and I was worried that the security guards were not going to cooperate, hence the story about the desk on the tenth floor. When the Seattle Room opened at 11am I told the librarian on duty an (abbreviated!) version of the plan and asked if I could leave my notebook there. She was not as enthusiastic as I had hoped, and she said that her shift ended at noon, so I might need to talk to someone else depending on at what time Elizabeth arrived, and she didn’t want to accept the notebook in the interim. I found a chair nearby, and waited. From each of my notebooks I cut out a hole just large enough to fit a small pen, and I put the ring inside and looped it around the pen’s clip to keep it secure. To ensure that Elizabeth opened the notebook, I texted her to ask if she could make sure an important receipt was still in the back pocket.

I had considered hiring a photographer to surreptitiously document everything, but it seemed too complicated and invasive, especially since the plan didn’t come together until the last minute. In retrospect I could have taken more photos myself, or set my iPhone down somewhere to record video, or even worn Google Glass, but I appreciated the time for quiet reflection as I waited for Elizabeth, and sometimes memories are best left to themselves.

We arrived at the library an hour or two later. While in the car, my mom and I reflected on how much had changed in the lives of each person in my family this year (she was preparing her annual holiday update letter for friends and family). I speculated with a chuckle, “Well, if Steven proposes before the New Year, that can go in there too!” My mom also asked a couple questions about the library’s architecture, so when we arrived, I encouraged her to find parking and we’d go inside together. She seemed disinclined, and thought that I should go in while she found parking. I hopped out at a red traffic light, and ran into the building while my mom continued around the block. The elevator to get to the tenth floor took a couple minutes, but because I had been there the day before I knew right where to go.

Angela called me after Elizabeth got out of the car, but I didn’t answer because I knew it meant Elizabeth was on her way up. I went back to the same librarian, who still didn’t want to accept the notebook but said that I could leave it on the desk. When Elizabeth stepped out of the elevators on the tenth floor, the Seattle Room would be on her right, so I ducked around a corner to the left towards the atrium outlook (pictured below left). While the elevators themselves have solid walls, the elevator bank has glass walls, so I could see when the elevators were going to arrive. Soon enough, one did, and I waited a few seconds before peeking around the corner. There was Elizabeth, walking the other way towards the Seattle Room, so I ducked back around the corner and waited a few more seconds…

Arriving at the 10th floor, I exited the elevator alone and saw the receptionist sitting to my right. There was the notebook! This had been so easy, I thought, and how nice of her to have it sitting out for me ready to go? I introduced myself and asked if I could pick-up the notebook. She seemed oddly curt and displeased, and she definitely didn’t let on that she knew what was about to happen. As I headed back to the elevator I quickly opened the notebook to look for the receipt that Steven had asked me to confirm was inside, and next to the pen there was a beautiful sapphire ring.

I slowed and vaguely began to understand what was happening. Literally the moment I looked up, Steven appeared from around the corner by the elevators, dressed in his suit. He looked wonderful, and I couldn’t stop kissing him. He then got down on one knee and asked me to marry him. I said yes, of course!

There was no one else around at that particular moment, so it was perfectly romantic. A couple minutes later another librarian offered to take some photos of us with Steven’s phone, and then we went outside and met my mom, who had been waiting in the car. The three of us went from there to a delicious lunch at the rotating restaurant in the Seattle Space Needle, making phone calls to family along the way.

After that we did some shopping in Seattle, went to Steven’s hotel near the airport to pick up his bag, and then drove back to my house outside of Tacoma. My mom dropped us off for a quiet celebratory dinner, and we also got to say hello to my grandparents.

Any number of things could have foiled such a delicate plan and left us with a less-perfect proposal story. We were lucky the whole thing went smoothly, but that’s negligible in comparison to how lucky we were to find each other in the first place!



Thanks to my parents Jim and Karen, my sister Amy, Elizabeth's mother Angela and brother Andrew, and my friends Jorge, Nina, Karina, Sukhjeet, and Anh for their support, input on engagement rings, feedback on proposal plans, and tolerance of my agonizing over details.

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