The Engagement Calendar – Operation: Root Canal

Spencer’s version of how it all went down:

Phase I: Planning for a ring

Over the course of our relationship, Judi and I had been discussing our long term goals and values. As things started to fall into place, the wedding date had already been picked, much to the bemusement of others who couldn’t figure out why I had not yet proposed. Picking the wedding date had as much to do with timing as anything else (it will be the day before our five years together), so it was only fitting that the proposal would follow similarly. When I landed my internship at AllianceBernstein in June 2007, I started to put away money for an engagement ring. My anticipation was that it would take at least the school year to continue saving up for enough money to afford a ring, coinciding with my graduation from business school and hopefully a solid job prospect.

The Friday after American Thanksgiving 2007, my mother, Judi’s mother, Judi, and myself went to look at the Waterview, in question of whether we would be book a wedding venue. We knew we were going to get married and that I was saving up for a ring–proposing was merely a formal step in between. Judi and I specifically wanted the date and, since it would be a holiday weekend, were concerned that delaying venue booking would not allow us our desired date. I know Judi’s mom had personal reservations, but Judi and I both knew that it was only a matter of time before the engagement anyway.

The morning after we looked at the Waterview, Judi and I were at my parents’ house. When I came out of the shower, my parents pulled me into their room and told me that when my grandmother passed away, she wanted me to have her engagement ring. After a lengthy discussion about the ring and what my options were, my plans were derailed. I didn’t have to use the ring, but it would be special to me. But what if Judi didn’t like it? What if she didn’t want an heirloom ring? What if the design wasn’t what she wanted? Would I keep the ring until May or would I use it and propose sooner? Could I keep my own secret for that long?

All of these questions started to fill my head, while at the same time, I just wanted to put some clothes on. Judi was still in my room waiting for me to get dressed, so when I finished talking with my parents, I headed back and entered….

Phase II: 42 days of deceptiveness (if you like Hitchhiker’s Guide to the Galaxy, maybe there’s symbolism here)

With the knowledge that I actually had a ring, I started to feel like Frodo Baggins from Lord of the Rings. Amazing power and amazing responsiblilty were to ensue. After we left my parents’ to head back to NY, this giant “thing” was hanging over my head. Over the next few days, I came to the conclusion that presenting Judi with a ring sooner would bode well for the element of surprise. In addition, I questioned my ability to keep my own secret of this magnitude for too much longer. So, I started to formulate my plan of action for a surprise proposal.

If you’ve seen the engagement calendar, you’ve probably remarked that my planning was meticulous. But it had to be meticulous because a lot of people were involved and I wanted it to be completely in character for everyone. I started to toss around the idea of ice skating as a good group function–Bryant Park, because it was free. Afterall, Judi and I somehow do those kinds of events with other people. Getting everyone into NY on the same day without her suspecting also became tricky; how do six people who are never in the same place at one time just show up in a city they don’t all belong in?

By the calendar, you may see that I figured it all out. Fortunately, everyone was willing to humour me. In addition, I had called the event “Operation: Root Canal,” in reference to the fact that I would be falling on the ice and feigning some sort of mouth injury. Since Judi would use my computer, I didn’t want her privy to correspondences concerning the proposal, so I required all parties to use “root canal” as a code word and filtered out all e-mails from my inbox.

In addition, I ended up needing to play dumb for myself, and have other people play dumb as well–hamming it up everytime we talked about the venue was booked, but she still had no ring. By December 8, her mother had gotten so wrapped up in the possibilities, that I ended up involving her parents in the charade. After seeing Cirque du Soleil at The Garden, we all went ring shopping and I was able to get Judi’s ring size. I called up my parents and told them to have their jewelers make the appropriate modifications (also changing the setting from 12 down to 4 prongs). When I started my winter break in South Windsor, I was able to pick up the ring.

For two weeks while in CT, I actually had the ring in my possession, making it all the more nervewracking. But I stayed in character and to my amazement, so did everyone else — planting their excuses just as I asked them. On the morning I went to Judi’s parents’ house, I had a small window in which I formally asked her parents’ blessing for the wedding (and apparently was informed that Judi’s two cats were the dowry). We’d even met with the rabbi and joked about not having a ring, yet I had to keep my mouth shut.

Judi and I headed back to NY on the 29th, just in time for New Year’s. On New Year’s Eve, we had gone to a party and joked that maybe I would be proposing like they do on Dick Clark’s countdown. So often over 42 days did I say that “maybe it’s coming now, maybe it’s coming in 5 minutes, maybe it’s coming tomorrow, it could be a week, it could be two weeks…” But alas, I’d other things in mind… and had stressed myself to the point where I gave myself a head cold.

So I was already sick on the day of…

Phase III: No longer “mythical”

The night before the proposal, Judi’s two friends Steph and Steph came into Grand Central and I met them at the train station. We went back to Queens and met Judi at Amish Market. For obvious reasons, I wasn’t overly hungry at dinner, though the four of us went to Doyle’s for some drinks. It was a relatively early night and by midnight, I doped myself to sleep on NyQuil and got a good night’s sleep.

The next morning I woke up, checked my bags twice to make sure I had the ring, packed up my ice skates, and headed to Grand Central to meet my friends Andrew and Carrie. Due to a visual mashing of numbers, I was 20 min late in meeting them, but we ended up walking to Toasties Cafe on 53rd and 3rd. We talked about what was to come and anxieties and things of that nature before heading to Bryant Park. The plan was that Judi and the Stephs would go to Dylan’s Candy Bar, Central Park, and then Rockefeller Center before meeting us at Bryant Park at 1pm.

Andrew, Carrie, and I went to the park and cut the line for our reservations. Judi’s friend Meghan had also called Judi to say that she was in the city and might be joining us. Then my friends David and Seth showed up. Judi’s friend Jess then showed up. And finally, Meghan and her friend Russ showed up. At that point Judi said to me “isn’t this weird, it’s like most of the wedding party is here today.” What a coincidence…

We got our skates on and when the Zamboni finished clearing the ice at 2:15, went on the ice. My friend Margaret had gotten out of her LSAT class and was on one side of the rink. Only two of us were actually skaters, but everyone else did surprisingly well. Andrew had grown up in CT his whole life, never went ice skating, but never fell once during the day — I was impressed.

Around 2:40, we had started to put in motion the final steps of the plan, although I still couldn’t figure out how to make myself fall. After taking a lap around the ice with Judi and Meghan, we were to congregate by Margaret under the watchful eyes of cameras. But Judi kept on skating. So then Steph, Jess, and I joined her but once again, Judi kept on skating. Finally, I skated up to her and said “ok, we’re going for one more lap.” With the ring on my finger in my pocket, we skated to where everyone else was.

I genuinely fell down–nearly taking Judi with me–but let my accident play out more real than could have been faked. I didn’t get up, but looked up and saw Judi just looking at all our friends. As I started to pull the ring out of my pocket, Judi still wasn’t looking at me. So I got up on one knee and drew her closer, saying “I know you weren’t expecting this until May, but will you marry me?”

At this point, I was in a zone, but Judi had doubled over laughing in disbelief. The crowd had already started to gather by us on the ice and was shouting “say yes!” Of course Judi said “yes” and everyone was cheering and hugging and clapping. A photographer from AM New York came over and took our pictures, a woman told us that her family was vacationing from San Diego and that her husband was a professional photographer and may have snapped a few pictures, and my parents called us to tell us they were in New Haven and on their way down to celebrate.

Phase IV: A new hope

Shortly thereafter, the ice was cleared off for the Zamboni again. We left Bryant Park and headed to a local bar for some drinks. At 5:45, we all went to Patsy’s Pizzeria on 3rd Avenue and my parents and my cousins Fran and Dave came to meet us as well. This was a pleasant surprise since they weren’t otherwise expected to make it to New York for the day.

We were there for quite a while and even ran into a family who was at the park when I was proposing. I gave Judi her engagement present (a diamond pendant) and we all got to talk and share the good news together over dinner with our friends. After dinner, we went back to the bar for a couple more drinks and then called it an evening.

The rest is in the books; the wedding date: September 6, 2009.

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