Tara Lee and Brian

Where to Propose in Upper West Side, New York

How We Met

As I watched the July 4th fireworks light up the Hamptons sky, little did I know that a few miles away, my future husband was doing the same. It was the summer of 2015, and while Brian and I would remain at different parties over that holiday weekend, our respective trips out east would prove to be the start of something very special.

We “met” on Happn, a mobile dating app, by which users cross paths with one another in real life and end up in each other’s dating pool on the app. Two swipes to the right and a few days of text messages later, we found ourselves laughing non-stop over drinks at the Ace Hotel in Manhattan. So, to be technically precise, we really, actually met after I got a little lost trying to find the Ace and calling him to come rescue me. But all the credit really goes to Happn.

How He Asked

Brian and I have a passion for antiquing; specifically, “treasure hunting” for political and patriotic memorabilia. I should say, Brian has a passion for it, and I’m slowly but surely coming around. Rarely does a weekend go by where Brian isn’t excited about a new potential item he found on one of his multiple estate sale apps, regardless of the city we find ourselves in. With our finds so far, some of my friends say we now have the smallest museum in New York City.

Wedding Proposal Ideas in Upper West Side, New York

So, on November 18, 2017, it certainly did seem like a typical Saturday morning when I woke up to Brian showing me a few screen shots of an antique federal mirror with a gold eagle on top that he found. We already had 5 of them, but this one was “very special, because it has candle holders.” Great, I thought, as I gave him a loving eye roll. But, as we also often do, we worked out a deal in which I traded joining Brian on this new treasure hunt in exchange for him fetching our early morning Starbucks and the promise of massages and pedicures after we checked out the mirror. It seemed like a good deal. It turned out to be the best deal, even though I never got my spa day.

Engagement Proposal Ideas in Upper West Side, New York

Proposal Ideas Upper West Side, New York

Everything about the subway ride to the Upper West Side seemed normal. So did the walk to the apartment building where the estate sale was going on. Upon our arrival, I noticed bright yellow signs for the sale, and we ventured inside to be greeted by the friendly purveyor. Brian made his standard rounds of the apartment, inspecting the available goods and glancing at the orange price tags that adorned seemingly every item in sight. I saw a few interesting items, including some decorative pillows, and Brian and I began chatting with the woman about those… and the mirror. It was around this time, while we had temporarily turned away from her to look at another item (at Brian’s suggestion, of course), that she disappeared though the back door of the apartment. “Where did she just go?” I asked Brian. He shrugged his shoulders, opting instead to use our newfound privacy to discuss negotiation strategy for the mirror.

Tara Lee and Brian's Engagement in Upper West Side, New York

After we decided on our price point, Brian took it upon himself to go to the back door and readied himself to open it. “Brian, don’t do that, it’s rude!” I loudly whispered to him. “Tar, come over this way with me, we’ll just go ask her quickly.” Brian isn’t usually one to make a faux pas, but I wondered if his antiquing passion was getting the better of his judgment. After several more attempts to cajole me over to the door, I eventually gave in, thinking that the sooner we got to the bottom of the eagle mirror decision, the sooner I would be laying face down getting my Swedish massage. And then, Brian opened the door…

“A lot,” Brian explained, when asked about how many Airbnb’s he had to look through, to find the perfect one. “It took quite a while.” This was not an estate sale, after all! The woman who greeted us at the door – she didn’t live there. In fact, she had never been in that apartment in her entire life until 15 minutes earlier. Nothing was actually for sale. And the eagle mirror? Brian had bought that months earlier. Once I realized what was going on, it was the greatest surprise of my life.

By now, you may have connected the dots – Brian had created a fake estate sale. He rented an apartment, in a nice, romantic neighborhood, that had an eclectic mix of interesting items, and an outdoor, private patio, nestled among buildings and rare city trees. And then he put everything in it up for sale. The eagle mirror was a plant, which he had kept in his office at work for weeks prior before adding it to the eclectic mix, and after doing so, he used his Photoshop skills so that the photos he took of it were morphed into the screen shots he showed me, seemingly from one of his antique apps.

So, when Brian opened the door, light poured into the room and my eyes widened to see a runway of rose petals that culminated in a circle on the private patio, with the “owner” of the estate sale now holding a camera pointed in our direction. Even then, it took me a few seconds to rid initial thoughts of “Ummmm, ok… these people are also having an event outside, in addition to their estate sale? Weird.” Once Brian took my hand and led me out on to the patio in the middle of the flower circle, and the apartment owner shapeshifted into a photographer who was now snapping away, it finally hit me. “I do!” I exclaimed. Brian’s knee then hit the ground, upon which I realized that it was supposed to be his line next. He then asked me to marry him, and I said yes for the second time in 10 seconds.

Brian was not without significant assistance in the endeavor, and we thank the amazing people who helped him pull it off. His scheme employed his parents, who kindly slept over in the Airbnb the night before, laid out the rose petals and put up the estate sale signs the morning of, and let the photographer in just before Brian and I arrived. The actual apartment owner graciously provided Brian with the timing flexibility he needed and fully supported the plot. The signs, and the price tags on the items, were made by one of Brian’s friends (to ensure they were in a different handwriting than his, naturally). The photographer, Jessica Iampolskaia of Forever Photography, truly went above and beyond, taking amazing photos but not before perfectly playing the role of estate sale salesperson, despite having never been to an estate sale before.

Brian and I now look forward to our wedding and spending the rest of our lives together. And I will happily be right by Brian’s side for all of our future treasure hunts!

Special Thanks

Jessica Iampolskaia
Photographer