A Snowy Proposal in Chicago

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How We Met: Melissa and I met back in the summer of 2005 while on an Alaskan cruise vacation. She was about to start her freshman year of high school and I, a year older, was entering my sophomore year. As an 8th grade graduation present, Melissa’s grandparents decided that they wanted to take her somewhere different, off the beaten path, and probably to a place where a 15 year old boy couldn’t meet and fall in love with their granddaughter. Luckily for us, my parents had the same idea and decided on Alaska as the perfect place for our family to get away from it all. Sometimes I sit back and think for a second about the astronomical odds we overcame just to meet. It had to be the same cruise ship, the same location, and the same week. Not to mention, in order to have any shot at a serious relationship after the cruise was over, at such a young age, we had to live relatively close to one another. It turns out we grew up just a mere 30 minute drive from each other and had never crossed paths until that week back in the summer of 2005.

The cruise liner was called Princess Cruises. While this sounds fitting for a love story, it turns out that this cruise is more geared towards the older crowd and is nothing like the Disney or Caribbean cruise ships where kids are the main focus. That being said, there was a place on the ship dedicated to teenagers called “Off Limits”. After getting settled on the first day, my sister and I thought it might be a good idea to check out this teen hangout center and see if we could meet anyone else our age. I will never forget walking through that door and immediately seeing Melissa sitting on one of the couches. Her gorgeous long blonde hair and beautiful baby blue eyes immediately made my palms sweaty and put a knot in my stomach. The first activity the teen center staff had us do was play a trivia game. We were told to get into teams and come up with a team name. I really don’t remember how it happened because I was so nervous at the time, but Melissa and I ended up on the same team and the rest, you could say, was history.

For the next 7 days, Melissa and I hung out non-stop. I remember waking up early (yes, a teenager waking up early on vacation) and staying up late in order to spend as much time with her as possible. I immediately fell in love with her personality. We would talk for hours, making jokes and laughing about the fact we had never met before. It felt as if we had been best friends for years. Before we knew it, the cruise was over and for the next 8 years we found ways to make our long-distance relationship not just work, but thrive. I can’t begin to tell you how many times I was told by friends that I should “try being single for a while” and to “meet new girls.” My response to them was always the same, “why would I give up someone who makes me happier than I ever believed that I could be and loves me for who I am, just to try being single.” This was truly one of those cases of love at first sight. And, the more that I get to know her as a person, the more I realized how amazing of an individual she is and how lucky I am to have her in my life. Her relentless work ethic, unconditional love for others, hilarious personality…. I could go on forever.

Looking back on our relationship, I find it hard not to believe in fate. How we met feels like a script from a movie and each day we continue to write a new page. While I may not be able to say what’s going to happen next, I am pretty confident that a cruise for the honeymoon will be in our future.

How I Asked: After graduating from college, Melissa landed a job as a traveling consultant. While a long-distance relationship was nothing new for us, knowing that I wanted to propose to her after we both had finished school posed somewhat of a problem as she was going to be in a different state every couple of days. As it turned out, December 14th 2013, marked our 100-month anniversary, and I could not think of a more special day to ask my best friend of so many years to marry me. I figured out from her schedule that during this time she would be in Chicago, Illinois and proposed the idea of me coming to visit her before she came home for the holidays. Melissa agreed without hesitation and immediately started planning all of the things we could do in the city together. Little did she know what I had in store.

I landed at O’hare International Airport on Friday the 13th only to be greeted by a snowy blizzard and below zero temperatures. While I probably would have complained about the freezing weather at any other time, there was nothing that was going to stop me from smiling from ear to ear that entire weekend. We woke up Saturday morning and the weather was even worse. We tried going to the top of Sears Tower and it was closed. We tried walking a few blocks to get coffee and Melissa got a leak in her boot. We tried hailing a cab just to get back to the hotel and there were no available cabs for over half of an hour, so we walked. At this point, I was getting nervous. It seemed like everything was going against us. But, if there’s one thing that Melissa has taught me throughout our entire relationship is to never give up on the dreams you have and the things you love. “Things have a way of working themselves out”, she always tells me.

Around the early afternoon the snow eased up and the wind died down. We thought that we would give it one last shot and walk downtown to check out The Bean and Navy Pier. I couldn’t have wished for more perfect weather. After taking some pictures and sightseeing for a bit, I asked Melissa if we could visit a park that I had read about online. Olive Park is a beautiful, secluded park hidden on the edge of Lake Michigan. The entrance is marked with a large iron gate that opens up to a long, tree-lined pathway out to a pier that juts out over the water with the Chicago skyline in the background. As we walked hand in hand down towards the pier, I texted Corlis and Megan Gray from GrayPhotography to let them know we were coming (I knew Melissa would want me to capture this moment so that we could share it with all of our family and friends).

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When we reached the pier, Melissa pulled out her phone and wanted to take a picture of us. I quickly grabbed her phone, put it in my pocket, and told her that I had something to ask her first. As we stood in the freezing cold with the snow falling all around us, I got down on one knee and asked her to marry me. I will never forget, for the rest of my life, that she actually never said yes. She immediately put her hands over her mouth in shock and could only manage to shake her head up and down. That was good enough for me!

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After we both wiped the tears from our eyes and pulled ourselves together, I pointed out the photographers to Melissa, who had been hiding a little ways away. Again, she put her hands over her mouth in shock, unable to comprehend how I was able to plan all of this without her finding out. We then spent the next 30 minutes taking pictures throughout the park. After making it back to the hotel, we then spent the next 2 hours calling all of our family and friends to share the news. I capped off the night by taking her to a steak house on the 95th floor of the Hancock building in downtown Chicago. As if the view from dinner was not breathtaking enough, our table overlooked the exact spot I asked her those four little words. It was an incredible way to cap off a day that we will both remember for the rest of our lives. I can’t wait to spend forever with Melissa and know that our journey through life together will be filled with many more amazing memories.

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Photos by Gray Photography