Ashley and Jason
Jason and I met each other while in the Bahamas February of 2012. I was on a vacation cruise with a friend, while Jason was staying at The Atlantis Hotel for a business trip. My friend had purchased two Captain Hats for us before the trip, thinking they looked funny and would be a good conversation starter. We put the hats on and decided to go to Atlantis for a few drinks. After being there for a short while, we see two guys on the opposite side of the bar get up and head our way. One of those guys was Jason. My friend and his friend immediately hit it off. They basically “picked each other” which left Jason and I there to entertain each other that night. We were all having a good time when someone suggested we head over to a night club that was inside the hotel. Once there, our friends continued to have a great time, Jason & I…. not so much. I wasn’t feeling well, so I was opting for bottled water after bottled water. Jason had already been drinking, and was in party mode. He was persistently trying to convince me to go dance with him, to no avail. After a while, he very bluntly asked me “Are you always this boring”? and took off with my Captain’s Hat to dance with other girls. Needless to say, our first impressions of each other were far from good!
Fast forward to September 2012, our friends who hit it off right away had been dating since that weekend in the Bahamas. My girlfriend would constantly tell me that I needed to meet Jason again, that he was actually a really great guy and was very nice. So, I flew to Fort Lauderdale from Denver to spend the weekend with her. Jason came over the second night, and we all went out together. He and I actually had a great time together, laughing, talking, dancing, and goofing around all night. We had such a great time together that we talked our friends into letting us tag along on a trip they had planned to Chicago two weeks later.
We showed up in Chicago and spent the entire weekend getting to know each other and exploring the city together. And as they say, the rest is history!
How He Asked: Because it was the place we first got to know each other, Chicago has always been special for us. So when I asked Jason what he wanted to do for his Birthday I wasn’t surprised when he said “let’s go to Chicago”. So, there I was thinking I was planning a nice Birthday weekend for him, all the while, he was actually taking me to propose. (Keep in mind, we’ve never really spoken about “marriage”, nor had we ever discussed or looked at rings.)
We woke up at 4 a.m. for our flights, so when we arrived in Chicago, we were exhausted. We went straight to the hotel and took a nap. When we woke up Jason wanted to go for a walk, which is what we do when we are there most of the time. I suggested that we go to the Navy Pier, and he said “let’s go!” We walked to the end of the pier, just like we did the first weekend in Chicago and stopped at the end right by a large Anchor. We always referred to it as “Our Anchor of Love”. We sat down on a bench by the water. I could see out of the corner of my eye that Jason was starring at me. When I noticed this, I asked him what was wrong – he was acting strange, but within a few seconds, I found out why! He stood up, got down on his knee and asked me to marry him! I said “YES!”. As soon as I had a chance to what fully grasp what had just happened, I started calling my family to tell them the news.
Jason reminded me that he had made us dinner reservations, and that we needed to head back to the hotel and change. While walking back we stopped to ride the Ferris Wheel, just like we did the first weekend we spent together in Chicago. Once we arrived back at the hotel we stopped and had a bottle of Champagne to celebrate!
I still didn’t know where we were going for dinner until he told the cab driver to take us to the John Hancock building. We took the elevator up to the 95th floor and checked in at the hostess stand. They took us to our table and as we turned the corner I saw Jason’s brother with a camera, then my best friend Mike, my sister, my dad, my mom and step-dad, my grandparents, Jason’s mom, his grandma’s, his best friend Rocco, and his brother’s fiancé Sophia.
Unbeknownst to me, Jason had been plotting and planning this day for months. While I was at work one day, he drove to Orlando to ask my dad for his blessing, he created a fake email account to keep everyone in the loop, he had sent itineraries, booked hotels, and created maps with boundaries to prevent us from running into each other and ruining the surprise. The amount of time and the attention to detail he put into planning our engagement is pretty incredible!
I am, and forever will be, blown away by how much thought and effort Jason put into making our engagement weekend such a special time for us, our friends and our families.