Jack proposed to his girlfriend Teresa on August 2 with the help of strangers at the Institute of Contemporary Art in Boston. Watch the above video to see the proposal play out. Below, Jack explains how he planned and executed his unusual proposal.
Teresa and I both knew we were going to get married eventually, although we'd never really said it out loud. (I found out later she was wondering if she'd have to sit me down and explain she wanted an actual proposal.) So, since I wasn't too nervous about the question itself, I decided to come up with a ridiculously complicated plan to worry about instead. When she suggested a date to the Institute of Contemporary Art (ICA), where we'd gone on our first date, it seemed like the perfect time.
I started scheming with my brothers and best friend. My idea was to inundate her with flowers from strangers -- first one or two, and then more and more, ending in the proposal.
I arranged to meet her at 6:15 p.m. on August 2 and walk over to the ICA for a picnic dinner. At the first phase of the plan, we arranged for a team of people she didn't know to follow her and give her flowers before she even met up with me. One of her friends at work let us know when she was leaving so someone could give her a flower right when she left. Then another one of our people started tailing her, so he could signal to a second agent to give her a flower on a random city block where she couldn't possibly think it was a setup. (You can see her turn down that flower in the video -- sorry, Jeff!)
I was lurking near the rendezvous point waiting to meet her. I got a text saying "She's coming out of work," and then nothing for 10 minutes. This was the moment I'd been waiting for for weeks, and I had no idea what was going on. Finally the guy tailing her sent me a text to tell me she was almost there.
When I met up with her, I wasn't even nervous -- it just felt right. I was happy to see her like I always am. I had a brightly colored umbrella and a fake picnic dinner. I needed her to carry the umbrella so strangers would recognize her. So I told her I saw it was supposed to rain, so I bought the first umbrella I could find -- why not use it as a parasol?
Meanwhile, my brothers (you can see them in tuxes at the end) had been handing out 300 pink and white carnations all along the waterfront and to the audience listening to the free concert at the ICA. We were about a mile away, so as we started walking only one or two people gave us flowers -- one of them a plant whose job was to text back to tell the band we were on our way. Teresa guessed that the flowers might be some kind of fraternity stunt or something -- she still didn't know I had anything to do with it.
When we got within about half a mile, I saw people I'd never met sitting here and there with flowers and they would get up to give them to Teresa as we passed by. (That's about where you can see us come into view from the camera we had planted in the 14th floor of a nearby building.) It's also where Teresa started to guess I might be up to something, although she didn't know what. I told her the flowers might be a viral marketing campaign.
On the last few hundred feet to the ICA, practically everyone we passed -- a few dozen people -- had a flower to give her. She finally knew for sure that this was something to do with her in particular, but still didn't know exactly what it was. She gave me the umbrella so she could use both hands to carry flowers.
At last we got to the deck of the ICA, and the second team of agents went into action. Their job was to intercept Teresa and slow her down long enough for me to do the quick change. She was instantly surrounded with friendly people offering her flowers. I walked away and met up with my brothers, who helped me into the tuxedo I'd cut up and velcro'd earlier in the week. A team of stagehands set up a bench and two trees loaned to us by a nearby garden store. We were ready to go in 15 seconds.
But Teresa was still surrounded with people giving her flowers -- I couldn't even see her. I sat on the bench and waited. By the time everyone was done, her arms were loaded with flowers, and she had no idea where I was. I crossed the deck and led her back to the bench under the trees.
After the proposal I had planned to whisk her away, because she's the kind of person who would want privacy after something like that. So we made our grand exit. The video kindly cuts out before I realized we were walking the wrong way and we snuck back through the cafe. We got into a waiting car out front and went out to a wonderful, hours-long dinner, where we mostly just kept staring at each other and laughing in disbelief. When we got home, my co-conspirators had wound Christmas lights and flowers around the spiral staircase leading up to our bedroom. We found out later that they were hiding behind a tree when the cab pulled up to drop us off.
Of course I wouldn't have proposed at all -- let alone in front of so many people -- if I wasn't pretty confident she'd say yes. And I knew that after it happened we'd still be paying the same bills and living in the same house more or less the same way. So this project kind of started because I wanted to add weeks of stress and anxiety to what was feeling too much like a looming non-event.
It certainly succeeded at that, and the engagement itself has brought us joy beyond words. But it's also been such a gift to share our joy with family members and friends and strangers -- to know that other people are joining us in that moment, and somehow believing in the crazy project we're undertaking. It feels like something we'll have to spend our lives living up to.
Maybe I'll look back at all this when I sober up and feel just a little silly. But for now ... well, we're over the moon. Thanks for joining us up here.