Claire and Matthew

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How We Met

Out one night at a local Naples restaurant and bar, we met through childhood mutual friend, Kyle Carufe. I noticed Matty right away and asked about him, shocked we didn’t already know each other already from growing up in the same town, having mutual friends and with Matty currently coaching with my uncle, Kyle was quick to introduce us. Although, we didn’t immediately hit it off. After the first night we met we continued to run into each other and then at another friend’s birthday BBQ we spent the day together and really hit it off. He walked over to say hi when I arrived at the party that day, and we then spent the rest of the day together; since then we’ve been inseparable.

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How He Asked

It was the most thoughtful proposal! It was Easter weekend so all of my five siblings were back home in Naples for the weekend. We spent the morning playing tennis with my older brother and his girlfriend and then I went to get my nails done with my two younger sisters. After our nail appointment we went over to the Waterside Shoppes for Starbucks and to walk around (little did I know this was all part of the plan).

After grabbing our coffee and visiting a few of our favorite stores my sister handed me a card with a handwritten note from Matty saying, “today is a very special day, go pick out something nice and I will see you at your grandparents.” I immediately burst into tears and looked up at my sisters in shock. Of course they got the whole thing on camera. We then headed to Lilly Pulitzer where they had organized a fitting room with dresses in my size and accessories to get a whole new outfit for the proposal! I was still in shock as I tried on dresses and my sisters made sure we stayed right on time to meet Matty at my grandparent’s house.

With a new dress, earrings, bracelets and a huge smile, my sister drove the 25 minutes to my grandparent’s and we sang and cried the whole way there; I was so excited but couldn’t actually say out loud what was about to happen. As we got closer to the house photos started appearing on the side of the road, Matty had lined the street with large, framed pictures of us from throughout the time we have dated. Matty greeted me in the driveway and held my hand as we walked down to the beach.

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When I got outside I could see my grandparent’s and extended family watching from the balcony. I couldn’t believe it! My grandparents mean the world to me but with my grandfather’s illness he is unable to leave the house, so Matty brought the proposal to them. As we walked to the beach I could see my family and a small laser sailboat. He asked me to raise the sail revealing the words, Will You Marry Me? He got down on one knee and I could not hold back the tears while saying yes!

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I turned around to a large cheer from the crowd of family watching.

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Of course his plan wasn’t over yet. With every thought out detail, from the sail expressing my love for the ocean and the sailboat I lived on as a student and teacher, to the sailboat necklace he bought me for my birthday back in December, it all came together as part of his plan. After pictures with my family and a visit with my grandparents we headed to my parent’s house for a full engagement party organized by Matty – catered and everything! I loved sharing the moment with family and being able to celebrate with my closest family and friends right after the big moment. Matty really went all out and made it a moment I will remember forever.

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Special Thanks

Dustin Prickett
Engagement photos
Jim Murphy | 
Proposal photos