Chicago Engagement

Our Proposal Story

I’ve never really told more than a handful of people how Ty proposed, but it’s a sweet story so I thought I would share! On Valentine’s Day of this year, Tyler gave me a letter that said to pack my bags because we were headed to Chicago that weekend. I was SO surprised and very excited! In the letter, he said to bring a fancy dress for Saturday and to get ready for a surprise on Sunday. All I could think was that he was definitely proposing on Sunday! What will I wear? How do I do my hair? How will he do it?! These thoughts started running through my head!

Saturday came and we were off to Chicago. When we got there, he surprised me by taking me to the Signature Room on the 96th floor at John Hancock. It was breathtaking! We were seated by the window with the most stunning view of the city. We dressed up, had an amazing dinner, then strolled through Chicago shops together. We went to Ghirardelli’s and split a chocolate shake, which we always do when we go to Chicago. Ty doesn’t love chocolate shakes quite like I do, but he always lets me pick the dessert (he’s a sweetie isn’t he?) Then we went to the Airbnb that Tyler had booked. It was just adorable—good find Ty! All I was thinking about is how he would propose the next day. I truly had NO idea! Ty was giving me no hints as to what the surprise was either.

Now before I get into this, I need to give you some background. One day, I was having a rough morning but had planned to go to Tyler’s house—this was about 5 years ago & in our first year of dating. I walked in and instantly started crying, he asked me what was wrong. He listened to me, hugged me and told me he had a surprise for me. He told me to close my eyes, and I opened them to him holding the newest Michael Bublé CD. I was SO overjoyed. If you know me, then you know he’s my favorite singer ever! I hadn’t heard his new CD yet and could hardly wait to listen. He told me he wanted to show me his favorite song on the CD that made him think of us. It was called “Close Your Eyes.” We listened together and of course, I cried again. It was such a beautiful song and in that moment, I could not believe how great of a guy I was dating. Ever since that day, it became our song. Nearly every time I listen to it I’m brought to tears. I love that it isn’t a very popular one, it isn’t trendy & it seems like one of those songs that kind of fell through the cracks…but it was the most special song to us.

Before we left for Chicago, Tyler asked me to bring my record player, as well as my Michael Bublé record so we could “dance the night away,” as the letter said. I thought nothing of it, as we sometimes like to put on Frank Sinatra or Michael Buble so we can slow dance. I have the sweetest memories of us dancing in my 8×10 dorm room in college. Tyler would grab my hand while I was mid-studying, turn on some music and start slow dancing with me. It would take all of my stress away, and we always giggled when I tried to sing along to the music… spoiler alert: I am not the best singer! But it always made him laugh and boy do I love seeing him laugh.

Back to Saturday night: Tyler set up the record player and put the Michael Buble record on. I was in my pajamas, with wet hair from a shower, and no makeup. We began to dance for about 3 or 4 songs… until our song came on. All the memories from that day in our first year of dating came back. I held him extra tight as we danced…and then Tyler started saying the sweetest things to me. At first, I thought he was just trying to be cute until I realized what was happening. I instantly started to tear up and was shaking my head. I couldn’t believe he was doing it…he was PROPOSING! He got down on one knee right as the song ended and asked me if I would marry him. With tears down my cheeks and the biggest smile on my face, I said YES!

See, this isn’t the typical proposal story, but I couldn’t imagine it going any other way. I always thought it would be photographed, I would be looking my best and people may be around to cheer when I said yes. But after it happened, I can’t imagine it that way. All the stress of looking good and making sure my reaction for the camera was good enough was completely gone. It was just us in that moment, doing something we always did that made us happy. It was the perfect proposal for us (good job Ty!). We went to sleep being the only people who knew we were engaged. We planned to go to downtown Chicago the next morning for a few photos to share with family and friends. It was fun having it be our little secret, even just for one night!

That surprise on Sunday I told you about?! Get this… Tyler rented out a jewelry store for us to hand-make his wedding band together… how amazing is that!? We spent Sunday afternoon making it from scratch. It was so so special.

I cannot believe I am marrying the most amazing man. He is perfect for me in every way. He exceeds every prayer I have ever had for a husband. I cannot wait for you to be mine forever Tyler James. Just 6 more months until we say “I do”!

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  1. Sarah says:

    This is so sweet!! I love the element of dancing because I hope that someday I’ll have a boyfriend/fiancé/husband who will dance with me!



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