Lloyd and Rachael

How We Met

Rachael and I had met a few times, briefly, through mutual friends prior to anything materializing. I went to UPenn and she went to Michigan. As is often the case with Jewish 20-somethings from the NY-tristate area, there was some always some serious overlap in our social circles. In fact, I went to nursery school with one of her best college friends, Dana, and have known her very well since I was 2. One of her other best friends from college, Anna, is married to my best friend of 23 years, Alex. I was actually the best man in his wedding while Rachael was a bridesmaid…before we ever went out.

Anna’s birthday is October 29th, so for a combination birthday-Halloween party in 2015, she invited a bunch of people up to her ski house in Vermont. Fun fact: I was only invited because I was dating one of Anna’s other friends (and bridesmaids) at the time. I was really leaning toward going to a different friend’s ski house for the weekend, especially as he was having a giant pig roast. Lo and behold, I found myself driving the girl I was dating at the time and a few of her friends 5 hours up to Vermont. Through a ridiculous sequence of events that have no real place in this story, that girl told me (the very night we got to Vermont) she took a job in Los Angeles. So, that was that.

Lloyd and Rachael's Engagement in Caveat - New York, nY

The next day, the group hiked to the top of Mt. Snow, and I spent a good chunk of the time talking with Rachael. It was tricky because she was also managing some work calls while on this hike, but there was some obvious chemistry. The semi-awkward, but kinda-cute chairlift picture attached to this submission was taken at the top of that mountain. That night, I was dressed as a hamburger and she was dressed as Mrs. Potato Head. We talked basically the entire night, non-stop. It was becoming even more clear that there was some real chemistry there. Finally, for the car ride home, someone made the executive decision of putting Rachael in my car, though for some reason the girl I had been dating was also placed in the back seat.

Rachael and I did not stop talking for one second in the car ride back. We talked about the difference in the type of “beauty” found in a sunset versus a Picasso painting, the fact that every car we drive by contains a group of friends or family that are involved in their own entire universe of experiences/emotions, and the way her family used to make jokes about crossing the Tappan Zee Bridge while saying that they were “tappin’ zee (the) bridge”. I was in love.

When I dropped Rachael off, I wanted a way to get her number, but there was some discomfort with all factors considered. We had been talking about the secret restaurant Bohemian, which does not have a publicly-available phone number. I told her that I had been many times and could text it to her…and I was in.

I got back to my apartment in Williamsburg (at the time) a little while later to find my roommate (Bennett) and his girlfriend (Katie) on the couch. They saw I had a beaming smile on my face and, before I even put my bags down, I told them I knew who I was going to marry. I was gushing about Rachael to Bennett and Katie, and also the rest of the world. But, it was a tricky situation because the girl I had just been dating was also one of Anna’s best friends and I wanted to be respectful. I figured I would give it a few days and then ask Anna if she was okay with me asking Rachael out. However, I’ve never been much of a patient person. Rachael and I were also talking about a pun-based improv show called Punderdome that takes place once a month. On Sunday, November 1st, I bought Rachael and I two tickets to the Punderdome show on December 3rd. I really don’t know what I was thinking, and I’m sure she was confused too. Apparently, one of her friends remarked that it would end up being our third date…which it was.

After two weeks of texting all day, every day, I finally secured Anna’s blessing to ask Rachael out and did so, successfully. In preparation for our first date, I did hours and hours of research. I even went and looked at some of the venues in person to see what would be best.

How He Asked

After that 3rd date at Punderdome, I started two things: I started putting money away in a mutual fund to pay for a ring and proposal, and also started a Google Doc with proposal ideas.

Rachael and I both love magic shows and had an awesome time at Chamber Magic (formerly at the Waldorf Astoria, now at the Lotte Hotel). My plan was to incorporate a magic show into our proposal. I had spoken to the magicians in charge of every major magic show in NYC and arranged to have Rachael called on stage and blindfolded and then there would be a whole thing with some magic words, she would be asked to visualize what she wants most in the world, etc and then the blindfold would come off and I would be on one knee. Amazing! Well, back in March, I needed her to check something on my phone.

When she opened the phone, there was an email from the magician saying, “you’re all set to propose at my magic show!” Obviously, my heart skipped more than a few beats, but I didn’t think Rachael necessarily knew that I saw this all unfold. So, I decided to make the best possible lemonade from these proverbial lemons. When it was time for me to actually propose with my new plan (details forthcoming), I had my dad email Rachael and I and say one of his patients offered him special, VIP tickets to Chamber Magic for November 10th, that included a private magic trick with Steve Cohen (the magician).

This threw her off pretty quickly. I also had some other wrenches thrown in – I told her, in advance, that I couldn’t get engaged before the World Series was over. Also, she knew that I wouldn’t propose with any of her family out of town, so I arranged for her to think her dad would be away on business over the weekend I was planning to propose.

There is a venue called Caveat on the Lower East Side of Manhattan. Their whole thing is “intelligent nightlife,” which is right up both of our alleys. We had first heard of it because a podcast Rachael loves, The Sporkful, was recording an episode called “The Bucatini Dialogues” there, where they discussed the best and worst types of pasta from a scientific perspective. We were quickly hooked on this new genre, and it sort of became “our place”. We went back next to the “Sloshed SATs,” which was basically an SAT-taking competition with a few twists.

Each audience member was given a real scantron with real Math, Reading, and Writing section to complete. However, there were performers doing stand-up routines and coming through the crowd during the sections, which made it a bit tricky. At the beginning of the event, they did a poll of the audience members to see who had scored the highest on the actual SAT when they took it. I was in the top 4, so I was designated as a “smarty” for the day and was brought on stage during each break. At one point, they asked the 4 “smarties” what their autobiography would be called and how many copies it would sell.

I thought I had a BRILLIANT idea…I said, “my autobiography would be called, ‘how I made $1 million off my autobiography’ and it would sell one copy..for $1 million.” No one laughed. At all. Except the host…kind of. I was later vindicated when the one person (in a crowd of ~50-60) who got fewer wrong than me was found to have cheated.

I knew Caveat had an event called Scratch Paper where people give mini-lectures teaching something from the sciences while weaving in comedy. I love speaking in front of crowds (yes…seriously) and spend an inordinate amount of time reading and listening to “nerdy” podcasts, so I thought I would be great. There is a particular theory I’ve always had about how “watching the weather affects the weather,” by way of two phenomena known as quantum entanglement and the butterfly effect, the latter of which most people have heard off. I had a great way to incorporate a proposal and was all set to do it on October 27th.

I hired a photographer and videographer and wore a suit with my favorite physics t-shirt. I’ll spare the scientific mumbo-jumbo (feel free to email me for more details) and cut to the end. After speaking about the ways in which small events can have ripple effects, I called Rachael on stage to “demonstrate” through a series of yes or no questions. You can see them in the video, but it was essentially a sequence of questions pointing out the unlikely chain of events that led to us being on stage, culminating with the question, “and, if we were not on stage right now, would I have an engagement ring in my pocket with which I’m asking you to marry me.”

In the video, you’ll hear her say “wrong hand,” but in my defense, she put the wrong hand out. I’ve known what hand the engagement ring goes on since I came out of the womb. Also, you’ll hear me say, “is that a yes?” In *her* defense, I never actually asked her to marry me. In fact, the answer to my question was technically “no”.

We had a Rolls Royce Phantom waiting for us outside. I had brunch reservations all over the city and Rachael chose Dirty French. We basically got one of everything on the menu but barely ate because we were so excited.

I had already packed a suitcase for her and had it waiting in a suite at the Gramercy Park Hotel along with some rose petals and bottles of Cristal. We went to Dear Irving for cocktails, then Rose Bar, and then had dinner at Gramercy Tavern. Finished the night with some late night room service (tiramisu). The next night, both of our families had dinner together in the private room at Union Square Cafe.

Our Video

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Special Thanks

Ash Fox
Photographer