I hinted to the story behind this hopelessly romantic photo in one of our very first blog posts… The guy on his knee proposing to this woman is Jake, and our guest blogger today. Jake’s proposal story is one of theeee coolest wedding proposals of all time. Enjoy the read!
“My wife is a very sentimental person and really loves pictures. We have scores of albums in our home that she enjoys going through from time to time. She would probably say that her most prized possessions are photographs. Knowing this about her, the idea of proposing to her and somehow getting it on film was born.
One of my best friends from college lives in Cleveland and he was willing to secretly tail Natalie and me as I proposed and take pictures of the days events. Because Natalie and I live in St. Paul, I thought it would be fun to kidnap Natalie for the day, fly down to Chicago, and propose to her in the WindyCity. My friend from Cleveland would then only have to drive half as far. He excitedly made the trip up from Cleveland to make our day really special.
The night before the big day, I told Natalie to be ready at 6 AM for a surprise “field trip”. Her excitement for the surprise field trip was curtailed by having great disdain for the early morning. Despite not being an early riser, she was ready to go on time.
After a quick flight from the Twin Cities down to Chicago our “engagement day” began. My friend Joey from Cleveland was awaiting our arrival at pre-determined breakfast stop called the Original Pancake House (Natalie’s favorite breakfast place). While we ate breakfast, Joey, whom my wife had never met, was sitting two tables away reading the paper and snapping a few pictures of us.
From there we ventured over to Lake Michigan and walked out onto a Pier. It was a beautiful clear morning and it was very quiet (probably because it was winter). Out on the pier Natalie and I talked for awhile which ensured that Joey would have time to get into position to take pictures. I proposed out on the pier and she thankfully said yes. Joey was able to capture the entire sequence of events from a great vantage point. Natalie didn’t have a clue.
For the rest of the day we meandered our way throughout the city. We shopped on Michigan Avenue, ate lunch atop the John Hancock tower and experienced Chicago together just a few days before Christmas. The entire day Joey tailed us and captured every moment with tons of great candid pictures. Joey even went as far as changing clothes multiple times to ensure that Natalie wouldn’t recognize this strange person who just happened to be everywhere we went.
After running around the city together for most of the day, we headed back to the airport to catch our flight home. As luck would have it, Northwest Airlines bumped Natalie and me up to first class for the ride home which was a nice touch. Upon arriving home, Natalie really wanted to head straight to her parents house to share all the details. However, I had arranged for all of our families and close friends to be at a restaurant in Minneapolis for a “surprise engagement party.” Natalie was thrilled about the party and was able to show off her new ring and share all of the details with her closest friends.
It truly was a fun, exciting day!
In Natalie’s mind, the day was over (albeit a great day) and now she could begin planning her special day. The next day, Joey sent me digital pictures of our engagement day. He had taken over one hundred pictures and did a marvelous job of capturing the day. I took these pictures and printed them out and created a hard cover book for Natalie. I wrote captions on each page and described to her where Joey was during each part of the day.
I gave her the finished product for Christmas (just five days after we got engaged). She was completely surprised and had absolutely no idea that we were being followed the entire day. She loves the book and had a great time sharing it with friends and family for weeks to come.”
Thanks Natalie and Jake for sharing your oh-so-romantic wedding proposal with the world!