Caitlyn and Jason

Wedding Proposal Ideas in Montauk, NY

How We Met

Flashback seven years ago, Jason and I met and we became us. It was 2011, I was 17 years old and Jason was 19 years old and in his first year of college. I had just started my first job at a sports bar, Miller Ale’s House, as a hostess and a few weeks later Jason started as a busboy.

One day in March, I was working an opening shift and had my first customers for the day. It was 11:00 am and we had only opened for less than a half an hour and not all of the tables were set yet, so I had to take the customers to the patio room on the opposite side of the restaurant. As I was done seating the guests, I was walking back to the hostess stand when an unfamiliar face with a Philadelphia baseball hat, who was setting tables, had caught my eye. I thought how cute he was and smiled at him as I walked by. It wasn’t much longer than Jason made his way over to the hostess stand to introduce himself and say hi.

Where to Propose in Montauk, NY

After that, he chewed my ear off and the other hostesses’ day in and day out. My good friend at work is the one who we should really thank for planting the seed in both of our heads that we should go out on a date. She had convinced Jason to text me and ask me out on a date. It was only a day or two later when I had received a text message from an unknown number saying “Hey Caitlyn, it’s your boyfriend from Miller’s”. After that, I had a pep in my step every day at work. I looked forward to the schedule for the week coming out, taking lunch breaks with Jason and just getting to spend time with him. My parents had picked me up from work one night and I remember telling them how a boy from work had asked me out on a date. Now, for everyone who knows me, knows that I never had a serious boyfriend and that Jason was my first actual “date”. My parents were skeptical of me dating an “older guy” (mind you he is barely 2 years older than me) so they had asked to meet him before he picked me up.

Proposal Ideas Montauk, NY

It was date night and I felt anxious and just the right amount nervous. I wore my favorite jeans, a coral tank top and my white Ked sneakers. Jason rang the doorbell and came in. His face was bright red and you could feel his nerves as adorable as they were. He met my parents, had small talk and we were off. We spent the whole summer together and we were inseparable. Fall came and Jason was off to college in Philadelphia. We dated long distance for four years as he was in Philadelphia and I was in New York and ever since then we have been together and now we will be together forever.

Caitlyn's Proposal in Montauk, NY

How He Asked

July Fourth 2018 was the day Jason popped the question of a lifetime. The energy was high and the vibes were chill. We were off from work for the week and we were headed out to Montauk to enjoy our vacation with friends and family. The weather was hazy and the temperature was hot. We loaded up the car and were off for a week of relaxation. Our first stop on the trip was to our usual lunch spot, The Lobster Roll (aka LUNCH) and we got our favorite lobster rolls.

We then strolled along the town as we waited for our condo, grabbed some beers at Montauk Brewery and soaked in sun. We made our way back to the condo and changed into our swimsuits and headed down to the pool. Jason’s mom, dad and two brothers were there with us shortly after we arrived. I was a little skeptical why they were joining us, as it was the Fourth of July and they normally attend a family party. I was thrilled they had decided to all come out, so I didn’t think too much about it. We talked, drank and laid by the pool. It was a great afternoon. Five o’clock rolled around and Jason told us that we all should start to get ready for our 6:30 dinner reservation at Gosman’s Dock.

Once we were ready, Jason said that he wanted to stop by the beach on the way to dinner and take some family photos of all of us together. I thought it was a great idea so I was fully on board with this. We get to our favorite picturesque spot and pulled over on the side of the road and headed over to the beach. The sun was in the perfect spot and the waves were softly hit the shoreline. I began to snap pictures of the gorgeous (almost) sunset and asked why no one was getting together for a family picture. As I turned around, Jason was on one knee and pulled a small black box out of his pocket. His hands were shaking and the ring box was upside down. I was completely and utterly speechless. He looked me right in my eyes and said “Caitlyn Margaret, I fell in love with you under the stars of Montauk…will you marry me?”. I truly couldn’t even believe what was happening and to have both our families there together made it so much greater. We cried, we laughed, we smiled and we loved. After that we headed to dinner right down the road. As if the night couldn’t get any better, my best friend of 17 years and her fiancé were there to greet us. It truly could not have been a more picture-perfect day.

When Jason popped the question…

Day after we were engaged…