How We Met
Our relationship began like most modern romances, via a dating app! Ironically enough, I matched with Brittany on the very first night I started swiping and never even spoke with another person on the app, basically batting 1.000! Due to busy schedules, we did not meet in person for nearly 2 weeks. I was incredibly nervous and may or may not have taken a double shot of tequila ahead of the meeting. We were both living in Boston at the time so I suggested we go to Beantown Pub as I knew they had pool tables so in the event the date went south, we had an activity to make things less awkward.
Brittany ended up being about an hour late due to work/traffic which meant I made friends with a few 50 something-year-old men and was three sheets to the wind by the time she arrived. Needless to say, the date went very well, we closed down the place and I vaguely remember sharing an uber and giving a side hug at the end of the evening as we bid farewell. Feeling incredibly hungover the next day I suggested we get a proper dinner that evening (power move), she accepted, we had a perfect meal and I sealed the deal with a real kiss. Since then we have lived in Boston, Chicago and Brooklyn adopted our pup Walter together, she took in the first love of my life my 10-year-old Jack Russel, Remy and the rest is history!
How They Asked
Here it goes! We have always talked openly about wanted to spend our lives with each other, having a family etc. Over the last 6 months, we began talking about marriage more seriously. I was pretty adamant I wanted her to propose to me first (this was all part of my cover plan to throw her off), so she was convinced a proposal was not in the immediate future. Several months ago I knew I had wanted to find the perfect ring and start the process. I am incredibly close with my family which meant they were heavily involved in finding the perfect ring. On the day I picked the ring, my whole family, including my two nieces helped, which made the moment even more incredible! I had gone through several ideas in my mind as to how I wanted to pull this off (I absolutely love surprises so knew it had to be BIG)! I finally settled on the apple orchard 1) because Boston is our home. We currently live in Brooklyn, NY and I knew we both would want to celebrate closer to home. 2) the orchard had a taproom, which comes into play later on.
I called the farm, walked them through the proposal idea and they could not have been more incredible to work with! I also asked a friend who does some photography work if she would help with set up and taking the photos and she too, could not have been more excited and incredible. At this point I had the venue locked in, next step was getting all of our friends and family in on the secret to ensure they were all waiting in the taproom immediately following the proposal, everyone was SUPER stoked and I made sure no one blew it my basically instructing everyone not to speak to Brittany for the month leading up to the proposal. Worked like a charm! Day of, Sarah (my photographer and creative director) went to the farm early to pick the perfect spot, set up lights and test the speaker which would be playing our favorite song.
All things were going great until it started to downpour. While we got soaked, it certainly lightened me up a bit and proved the farm was the most gorgeous location despite the rain. Brittany would be taking the train in from NYC later in the day so we were able to set everything up freely. I also instructed my family to arrive early and “drop the hammer” to ensure everyone was hidden and ready to roll once I set the text that we were on our way back from the proposal itself! Once Brittany arrived I told her I had a surprise to kick off our weekend back in Boston, this wasn’t unusual as I mentioned, I LOVE surprises, she actually later said she thought to herself, seriously another surprise?? When we arrived at the orchard she was super excited to pick apples, although she quickly noticed the farm was technically closed.
This was by design so we had some privacy but she refused to get out of the car to avoid having anyone on the farm work late to accommodate us, mostly I think she wanted to go get a beer but I convinced her we would be quick and it would be like we rented out the place! She had no idea at this point and was taking photos and joking on Instagram that I rented out the place (that is an exceptionally funny video in hindsight). I began walking us further into the orchard walking past countless rows of apples. Brittany somehow was still none the wiser as she snapped photo after photo. As we continued walking hand in hand the music started getting a bit louder. I had mentioned earlier in the evening that there would be a band at the taproom so she assumed the band was playing in the orchard….(how she didn’t start to get a clue at this point was beyond me). As we started to round the corner to THE SPOT, she finally realized The Few Things by JP Saxe was playing, this is our favorite song.
When I didn’t say much she started to piece things together. We rounded the corner where she saw the lights and it FINALLY hit her! She immediately lost it. I told her all of the reasons why I love her and of course, asked her to marry me. Given my nerves, I forgot to take the ring out and after she said yes, she said well can I see it?! I put the ring on her finger, Sarah popped out and continued taking photos we will have forever. The surprise wasn’t yet done, so I suggested we get a beer (clearly I had earned it).
She thought we would grab a beer with Sarah and tell all of our friends and family via FaceTime/phone etc later in the evening. We made our way to the tap room, and as we entered all of our friends and family were there waiting to finish off the most perfect evening of our lives. She absolutely lost it again and I finally could relax!! We celebrated with the people we love most and truly had the best night of our lives. The day after very closely resembled the day after our first date, we were both incredibly hungover and even more in love than the day before.