Ashley and Jon

Marriage Proposal Ideas in Montauk, NY

How We Met

Jon and I met back in June 2009. I was interning for the finance company that my dad works for on Long Island when Jon began working there. I can honestly say it was love at first sight for me! He was the most gorgeous man I had ever seen and I knew from that second I wanted to date him and eventually marry him. We were friends for about seven months before he finally asked me on a date. He had been super hesitant to go out with me since he works with my dad and didn’t want to ruffle any feathers. So, he called my dad to ask permission to take me on the date and my dad’s exact words were, “Jon, please take her out. I’m sick of hearing her talk about you at home.” So with my dad’s (hilarious) blessing, we went on our first date and the rest is history!

Engagement Proposal Ideas in Montauk, NY

How He Asked

On the weekend of September 17th, Jon and I were in Montauk, NY for a friend’s wedding. We woke up that Sunday morning and had plans to head to a vineyard before going home. We had some time to kill before they opened, so Jon suggested we take a walk around the Montauk Lighthouse. Visiting the lighthouse is actually one of our traditions, so I didn’t find it unusual at all when he suggested it!

The lighthouse is where we first said, “I love you” back in 2010, so we always try and make it a point to stop by and take a walk around it when we are in Montauk. We spent about 45 minutes watching the surfers and skipping rocks on the water before he turned to face me and told me he loved me. I STILL didn’t know what was happening and naively responded, “Aw, I love you too babe” and tried to give him a hug.

He held me still and once he kept going with his speech it occurred to me what was going on. Once I saw him get down on one knee, I immediately started to tear up and when he proposed I couldn’t say yes quick enough! However, the night before, Jon had a dream that he dropped the ring down in the rocks and lost it so he didn’t want to touch it! We both kept staring at the ring until I finally went to grab it to put it on and he just kept saying, “Be careful, be careful!” Unbeknownst to me, Jon had also hired a photographer to capture the moment and to do a whole engagement photoshoot after.

Ashley's Proposal in Montauk, NY

After leaving Montauk, Jon told me that we were going to have dinner at our country club with my parents and his mom. Turns out, he and our moms had coordinated a whole surprise engagement party! As we were walking up the lawn, I saw the faces of about 50 of our closest friends and family and started crying – again! I couldn’t believe how much planning and effort everyone put in to make the whole day absolutely perfect – and that nobody accidentally spilled the beans!

Special Thanks

Heather King Photography
Photographer