Sherry and Christopher

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How He Asked

Every proposal story is beautiful, I consider mine and Chris’ one of my favorites. Chris and I were extremely excited to book our second trip back to Disney. We had gone two years before and fell in love with the overall magic and excitement of it, obviously. When arriving, I felt happy to be away with Chris. In today’s world it is easy to become caught up in everything going on around you and this trip gave us an excuse for some much needed time off to enjoy each other. Upon arriving, Chris had mentioned he made a reservation at Mama Della’s that night. I thought nothing suspicious of this as this restaurant already served a special place in our hearts.

sherry's Proposal in orlando, florida

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On our first trip to Disney, we enjoyed a meal here. I remember us both being enamored by the hotel’s beautiful architecture that resembled the Portifino area in Italy. The restaurant also reminded us of a cozy warm Italian home in the country side of Italy that also happen to serve excellent an authentic food! Like any smart man, Chris had suggested we get ready two hours before the reservation. He said he wanted to give me enough time so we can walk around and take pictures outside the restaurant by the water prior to dinner. Being that it was our first night I wanted to dress up in my best outfit! I remember putting on my new favorite long black maxi dress from lulus and although I felt a little over dressed, Chris insisted it was perfect for the night. After getting ready, we walked down to the lobby of our hotel and called for a bicycle trolley.

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Not long after, we got on the trolley and were off to the Portifino Hotel. Chris was acting so normal and I was completely unaware of what was about to happen next. When arriving at the hotel we stopped short of the restaurant so that we could enjoy the scenic walkway and enjoy the picturesque view. When we got near the water Chris asked if I wanted a picture taken with the beautiful hotel behind us. Once I said okay, he started to take out his camera so we could take a “selfie”. As he did, a couple nearby who appeared as tourists asked if we wanted them to take a picture for us, instead of the selfie. Chris immediately said sure and handed the supposed stranger his camera. As the couple stood there taking a photo of us, Chris got down on his knee!

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He then started saying how much he loved me and recited the most beautiful words. I then knew this was the moment every girl dreamed of and here I was trying to take it all in with complete shock! Once I said yes, Chris got up and kissed me! He then explained to me he hired the couple who acted as tourists to take pictures of us through a company he found online called “Fly-tographer”. They too were in on the proposal and had planned the whole proposal setup so that they could capture the moment!

Chris then explained the photographers were also hired for the next hour so that we could have an engagement photo shoot as we roamed the Italian piazza grounds. For the next hour we spent our special time getting photographed around the beautiful hotel as if we were celebrities and the photographers were the paparazzi while onlookers congratulated us.

Afterwards, we walked into dinner where the restaurant had been expecting us. Once we were brought to our seats, we had chocolate covered strawberries, champagne, and a beautiful bouquet of yellow flowers waiting for us. Everything was so beautiful and well planned by Chris.

To cap it off, during our dinner we had an older Italian man sing Italian songs and playing the guitar while we ate and tried to soak it all in. The night was absolutely magical. The rest of the week we continued our celebration at Disney. The magic never stopped. Everything that entire week was so beautiful and with little surprises that crept up everywhere. Chris is a special man and I am very lucky to be his fiancé. We are definitely enjoying the moment but couldn’t be more excited about our future!