Stephanie and Matty

How We Met

Matty and I grew up together in a small town south of Boston, MA. We were good friends all through middle and high school; he was the guy that threw all the parties and I was the girl who loved to party! I remember when we were 13 years old, staying up late talking on the phone together f or all hours of the night. He was different than all the other guys, and I knew it from an early age. He was the people-pleaser, but not in a way that let others take advantage of him. He was always the most fun guy in the room, constantly surrounded by friends and making everyone laugh. But what caught my attention the most was the way I was able to trust him wholeheartedly, even at just 13 years old. He always made me feel so comfortable when we were together, even through those awkward teenage years. When we were 15 years old a few friends were hanging out in his pool house for a casual Friday night. It was the same night he broke his elbow (for the second time!). I remember thinking to myself early on that night, “Why do I feel this way about him? Sure, I’ve had many crushes before, but why does this feel so different?” I was too young to understand what those feelings were, so I put them in the back of my mind.

Fast forward to our senior year in high school- When we left for college, we kind of drifted. He went to the University of Colorado- Boulder, and I attended the University of Massachusetts- Amherst on the east coast. We’d occasionally exchange texts over the semesters, and meet up again over breaks, but nothing more since he had a girlfriend and I was dating someone as well. After college when we were both single, Matty ran into some of my besties at a bar who knew I (always) had a crush on him. They “casually” mentioned where I lived and found out he was living in the next town over, less than 5 minutes away from me! I got a message the very next day asking to grab drinks at our local bar. When I walked into the bar that following week, seeing him sitting there, my nerves were out of control! I was older now, and I knew what those feelings that I’d been harboring for all these years had finally meant. Fast forward through the best six years of my life, we’ve moved across the country together, got a puppy named Gordon, and have been each other’s support system through everything life throws at us! People always say “when you know, you’ll know” and it couldn’t be more true. I’ve known since we were 13 years old that he was the guy I was going to end up with, and I couldn’t be happier!

How He Asked

I was the girl that thought about my proposal all day EVERY day. I knew he was the one I was going to marry, so in my mind I did not want to wait a second more. I also thought I would be the girl who had to fake the surprise aspect. There was no way he could plan a proposal and I wouldn’t find out about it! We had plans with our mutual friend, Tyler, and his new girlfriend, Eliza. Tyler is in the hospitality industry and Eliza is a food blogger, so it made sense that we had a few fancy dinner reservations lined up, then a trip to Napa planned for Saturday. Eliza was going to write a story on this exclusive winery where Tyler had set up a tasting at. A car service had picked us up that morning (I was told because since Eliza was covering a story at the winery, and they wanted to give her a complimentary service). We pulled up to the most beautiful winery I’d ever seen. The lush green vineyards in the background, mixed with the historic neutral colors of the winery was something I’ll never forget. It was 100 degrees that day, and all I kept thinking was how silly it was that I was wearing jeans. Kassandra, our host at the winery, came out to greet us, and spent the afternoon giving us a private tour of the grounds and finished with a relaxing tasting inside. When we were done, Kassandra asked if we wanted to take an off-road drive further out and see some beautiful views of the water. Of course we jumped at the opportunity! We hopped in her 6 passanger ATV and got ready for a fun little adventure to see the acres. The whole ride up, Matt kept telling me how much he loved me. I thought it was a little strange, since we weren’t exactly in a romantic environment as the ATV can be super rough and bumpy! When we pulled up to the spot Kassandra took us to, my mouth instantly dropped. The views were unlike anything I had seen before. We were at the top of the mountain overlooking Carneros and San Pablo Bay, and in the very distance you could see San Francisco! I was loving the views, and didn’t hesitate to take out my phone to snap a few selfies! All of the sudden, Matty pulls me towards him, and with his hands shaking, he tells me how much he loves me and I could tell he truly meant it. He then got down on his knee, pulled out a ring, and told me he promised he’d take care of me forever, and forever started today. I was in COMPLETE shock. I couldn’t form words. All I kept asking was, “Are you serious Matty? Are you lying? Is this a joke? Tell me the truth!” After screaming “YES!” and crying into his arms, I looked over and saw Tyler and Eliza had been videotaping the entire proposal.

Stephanie's Proposal in Napa Valley, CA

Marriage Proposal Ideas in Napa Valley, CA

Little did I know, there was no story Eliza had been covering for work. This was all a setup that everyone had been in on to get me to the winery for the best day of my life. Matty told me not to make any phone calls yet, and just enjoy the moment together. We headed off to lunch at a hotel rooftop bar in Napa, about 10 minutes away. When we got up to the rooftop, the four of us were deciding where to sit. Out of nowhere, my mom, sister, and a bunch of friends had jumped out and yelled “Surprise!” My family had flown in from Boston to surprise me for this special day, and it brought me to tears all over again! I was in complete shock, yet again. The surprises didn’t stop there. After I was finally able to calm down and take it all in, Matty told me he bought us tickets to go home to Boston next month for a big engagement party! My heart was about to burst. My roots- my friends, my family, everything I knew was in Boston and he knew well enough that all I’d want was to be able to celebrate back home. I can’t believe after six years of dating, I’m finally able to call him my fiance! He is the love of my life- and I’ve always known it was him.