Cathy and Matt

Engagement Proposal Ideas in Greenport NY

How We Met

Matt and I have been together for almost thirteen years. We started dating in eighth grade when Matt asked me to be his girlfriend over an AIM instant message, and have been by each other’s sides ever since. We won Homecoming King and Queen our Freshman year of high school and Class Couple when we graduated and went on to earn our degrees from Stony Brook University in 2016.

Marriage Proposal Ideas in Greenport NY

Our time together has been filled with amazing memories and traditions, formed as we both matured as individuals and a couple. We love to explore each other’s interests, like concerts and Broadway plays, hiking and cooking, traveling and volunteering. We are absolutely thrilled to be engaged and excited to continue intertwining our lives together.

How They Asked

Matt and I have a tradition of taking a quick vacation in December to recharge before the holidays. When Matt suggested we head out to Greenport the first weekend of December, I thought nothing of it. His travel schedule for work was pretty full that month, and he said it would be a good time to take our “stay-cation”. I had a feeling something special was going to happen when Matt took the initiative to book the Lin Beach House and make a brunch reservation at Jedediah Hawkins Inn. We drove out to Greenport Friday evening, had dinner and drinks and relaxed back at the hotel. The next day we took a ferry over to Shelter Island to hike the Mashomack Preserve. It was a beautiful winter’s day, the sun shining and cool air on our faces.

We grabbed a coffee on our way back to the hotel and got ready to meet up with friends for dinner. Matt mentioned there was a beach at the end of the block we were staying at and he wanted to catch a glimpse of it around sunset. It seemed like a normal suggestion to me, so we headed on over. Once we pulled up and started walking down the 67 steps to get to the beach, I noticed the twinkle lights everywhere and what was waiting for us at the bottom- a whole setup with a blanket, candles, and photos of us throughout the years! Matt helped me down the steps (as I was already crying and shaking at this point!) and guided me to a spot on the blanket.

He got down on one knee and pulled out the ring we had designed together months before. He asked me to marry him and of course, I said YES!!! As we hugged I heard screams from behind me- Matt had invited a bunch of our closest friends to be there to celebrate with us!! Some had been there hours before to help set up (shout out Debbie, Amanda, and John!). After lots of hugging and crying, we headed back to the hotel to celebrate with champagne and pizza. We were so touched that so many of our friends came out to spend this time with us. We ended our night by visiting The Custer Institute and Observatory to take a look at the night sky. It was a perfectly romantic way to end our special day.


I found inspiration from Jessie Kuruc and Lauren Priori, both of whom I had found on Instagram. I had sent many photos to Matt explaining how I wanted a unique ring, similar to the Ellie Ring Jessie had designed. Matt wanted the ring to be exactly what I dreamed, so he set an appointment for us to visit Lauren’s studio in Philadelphia. We drove out there one Saturday in February and had a WONDERFUL meeting with Lauren who helped us design exactly what we were looking for. Once I approved the design, Matt kept the ring hidden and the first time I saw it was when he was down on one knee. The ring is a 2.65ct cushion cut green unheated Montana sapphire set east/west with two rose-cut pear-shaped diamonds on the side, all set in white gold.