Michelle and Jonathan - The Best Chicago Marriage Proposal You'll Ever Watch

How We Met: Jon and I are southerners who came to the Windy City to pursue our careers, but had no idea that we’d meet our “person” in Chicago too. We were at a mutual friend’s party on a Friday night, and I went up to introduce myself.


Everything about him was intriguing to me, from his fu manchu (which I later found out was just a joke… thank God) to his eclectic taste in music, to his weird and wonderful sense of humor. He pursued me the way every girl deserves… he sent me flowers, took me on extravagant, well-planned dates, sent me emails every morning before I got to work (and still does), and was one of the best listeners I had ever met.


Of course all of this was surface-level and amazing, but then I eventually learned what a family-man he is, what he values in life, and how serious he is about growing in a relationship with Christ. It was pretty much a done deal after that :)


how they asked: I’m not sure if you would call this a “proposal” or a a highly choreographed stealth operation. Pretty much every person in my life knew about this for several months leading up to it, and nobody said a word. I don’t know if I should be impressed or concerned.


It was Saturday, July 26th and we were going out for brunch and mimosas in Chicago. We were having a great time when he suddenly got up from the table to go to the bathroom… for a third time. Only this time, he didn’t come back. I felt a tap on the shoulder and when I turned around, my 2 sisters who live in Atlanta were standing there!! I was completely shocked and didn’t even know what to say… and of course crying was involved. They had a note from Jon and a clue for where I should go next.

The next thing I know, my 2 best friends from work pull up in a car to take me to my first destination – the first place we met. When I get to the apartment (where we met at the party), my Chicago friends are there to greet me and give me my next clue: to go to the place we had our first date. My best friend from Nashville and my best friend in Chicago are waiting at the restaurant with more mimosas and food! I was really crying at this point.. and not pretty-crying.

My next stop was to go to the Chicago Theatre, which is where we’ve had some of our favorite dates. When I arrived, his sister, brother-in law, and uncle were all there from Raleigh, NC! I was completely shocked… and surprise surprise… was crying again. They all gave me sweet notes and sent me on my way to Wrigley Field for my next clue. It was a crowded day in Wrigleyville for the Cubs game, but I saw my mom from a distance and lost it. All of our parents were there waiting with hugs, sweet notes and more tears.


The final clue was to go to Diversey Harbor, which a place we like to sit and look out at the water. The whole group from the day was there, and Jon came out from around the corner with the final note. “I just have one last thing to ask you”. He got down on one knee, proposed, and gave me the most beautiful ring I’ve ever seen.

Best Chicago Marriage Proposal

He then told me that we had an engagement party to go to directly following… casual.

Best Chicago Marriage Proposal

After celebrating at the party with some deep dish pizza and wine (he knows me so well), we made our way to a street festival with the entourage in-tow. After that, Jon had rented out a bar/bowling alley and we partied until last call! Not even sure the wedding will top this day :).

Best Chicago Marriage Proposal

Best Chicago Marriage Proposal

Photos and video by: 84 Degrees West (Alexis Taylor)