Surprise Proposal in Chicago

What’s the recipe for a perfect proposal? We recommend taking cues from this clever groom-to-be. By enlisting the help of trained professionals and picking a romantic waterfront location, he surprised his girlfriend with a heartfelt proposal set to her favorite songs performed live. Every detail, from the proposal playlist to the timing of events, was thoughtfully planned. We’re not the least bit surprised that she happily accepted. We congratulate this lovely couple on their engagement and wish them the best.

How We Met:

When I woke up one Sunday afternoon in February 2011, I was hung over, hungry, and lazy – the triumvirate of bad combinations. As the popular saying goes, “The best cure for a hangover is the hair of the dog that bit you.” I met some friends at a local watering hole, and we recounted stories from the previous night. As more friends and acquaintances joined us, I was later introduced to Kristine and her friends. Kristine and I discovered that we lived in the same apartment complex; specifically, Kristine lived exactly three floors above me. When it was time to leave, I found out that Kristine had “accidentally” paid for my meal. I texted her and thanked her for the meal and promised to cook her a steak dinner. And then she friend requested me on Facebook. (Sidebar 1: We still debate on who friend requested who first, and I am 99.5% sure it was her.)

When I met Kristine, I had sworn off all relationships for at least two years. I was still sour from the prior one. However, Kristine changed my negative mindset shortly after we met. In the following days, weeks, and months, we spent more and more time with each other; and I grew more and more fond of her. We just clicked. I thoroughly enjoyed every minute hanging out with her, whether it was watching television, going for runs, or hanging out with our respective group of friends. In addition, she actually enjoyed spending time in my bachelor man cave, which was a small one-bedroom apartment with stained cement floors, dark and modern furniture, half naked lady paintings, and beer. Her ridiculously good cooking (Sidebar 2: All my friends can back me up on this one) made me blow up from a frail 145 lbs to a portly 165 lbs in a matter of weeks. The relationship weight was here to stay (Sidebar 3: Sadly, All my friends can also back me up on this).

Planning the Proposal:
Time flies when you’re having fun. Our one-year anniversary came with the quickness. I decided to propose to Kristine when we booked our trip to Chicago to celebrate this occasion. With the help of her best friend (and now Matron of Honor), I customized her ideal engagement ring. Meanwhile, I enlisted the help of Shakira  ( Fairytale Weddings & Events), Doris Torres (Doris Torres Photography), and Denita Waugh (Independent Musician) to help plan the perfect proposal. Since I had never been to Chicago, these three helped me pick a spot that would be somewhat public, close to Lake Michigan, and have a clear view of the Chicago skyline – Theatre on the Lake.

The Big Day:
On the day of the proposal, Kristine and I spent the whole day walking the Magnificent Mile and visiting the Hancock Tower and the Lincoln Park Zoo (Sidebar 4: I saw a polar bear for the first time and it was awesome). During the hours leading up to the event, I texted back and forth with Shakira  and the team as they secured the public area and set up the location. Once that text from Shakira  arrived telling me the lighting was perfect, time started slowing down for me. My palms got sweaty. My voice got shaky.
It was time.

This is it!
When we arrived at the rocky area, I pointed out the “random musician (Denita)” to Kristine, and we walked over and listened to what she was playing. After a few minutes of guitar melodies, Denita went into the first planned song – Jason Mraz’s “You and I Both.” Kristine was very surprised, as this was one of her favorite songs. After the song finished, I asked Denita if she “took requests” and “requested” Dashboard Confessional’s “Hands Down.” She happily obliged (Sidebar 5: Denitadid a great job learning this song in two weeks) and started the song.

By this time, my heart was beating out of my chest. I didn’t expect to do this when initially planning the proposal, but it just happened. At the start of the second verse, I turned around and started singing to Kristine. I also changed some of the lyrics to reflect how Kristine and I first met, how we grew closer, and how we were going to spend the rest of our lives together.

Near the end of the song, I reached into my pocket, grabbed the ring out of its box, got on one knee, and proposed to my future wife. She said yes! At this point, Denita started playing the third planned song, Jason Mraz’s “I’m Yours,” which was another one of Kristine’s favorites. Before, during, and after the proposal, Doris Torres was “discreetly” taking photos of this whole even. I had him tell Kristine that he was taking pictures for Denita ’s portfolio, and he just happened to be there at the perfect moment.

Thank You.

I would like to thank Shkira, Denita , and Doris Torres for being very flexible and making themselves available for the proposal planning. This would not have happened in such a flawless manner without their help. (Sidebar 6: I must also mention that my only public performance would not have happened had I not taken vocal lessons from Amy Sardone. At the time, I was just taking vocal lessons to learn how to sing. I had no idea I would be using this “talent” to propose to my future wife.)