Courtney and Jason

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How We Met

I moved to Los Angeles after growing up in Texas and graduating from college to work in the entertainment industry. After about a year in LA, I met Jason who at the time was a fellow assistant at the film studio we both worked for. We became friends first, and it was a spur of the moment road trip that we randomly decided to take for the 4th of July holiday a year or so later, that made us realize how much we enjoyed each other. A few months after the trip we officially became boyfriend and girlfriend and we have been inseparable ever since.

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How He Asked

In June 2016, we went on our dream vacation to the Amalfi Coast and the Greek Islands. We spent a few days in Capri, Italy before heading to Positano, Italy – one of the most magical places I have ever been.

Jason had planned to propose on our second night in Positano but we woke up to a full day of rain in the forecast. Jason secretly had to email the hotel, photographer and our families to push the proposal a day, all without me thinking something was up and while I nagged him for being on his phone too much. Our last evening in Positano, Jason told me we would be going to the nicest hotel in town because it had the best view and a lady at our hotel just so happened to be married to the sommelier at the hotel restaurant and would hook us up with a reservation (he made this all up so I wouldn’t get suspicious of having to dress up.) We spent the day at the beach and then got all spruced up for cocktails and dinner. I didn’t notice then, but Jason tried on 3 variations of white button down shirts before we left due to his nerves and even snuck down to the lobby bar for a shot of whiskey.

We went to the Il San Pietro Hotel in Positano and they had the corner bench with the most incredible view of the coastline held for us. Jason had been coordinating everything with the hotel and a photographer for months. The hotel must have been just as excited and nervous as Jason because they accidentally brought out a surprise envelope a little early with our cocktails and he had to make his move. He asked me to stand up and pulled me to the front of the bench. I can’t remember anything he said I was so overwhelmed with happiness! He got down on one knee and I don’t even think I let him finish asking the question before I said, “YES!”

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He then pulled the surprise envelope off of the table and handed it to me telling me that he knew how much I would have wanted my family to be a part of this special moment so he had booked us a flight home for 4th of July to celebrate with them and my closest friends. He thought of every detail to make it the most magical and perfect night. We had dinner at the fancy hotel restaurant, drank expensive champagne, and ordered an entire cheesecake by accident before we went back to our hotel to call our parents and tell them the news. Jason planned the proposal in Italy so that we still had a week of our vacation left in Greece to celebrate – the next week we got to explore Mykonos and Santorini as fiancés!

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