Natalie and Tim

Where to Propose in Chicago

How We Met

Tim and I met thanks to modern technology, Tinder! One faithful December I was out with friends having dinner and the topic of dating came up. After a few stories of horrible dates, we all took out our phones to browse Tinder. After a few swipes left, Tim’s photo came up. It was a photo of him crawling through mud ( he was doing a Spartan Race) and I was instantly intrigued. I swiped right and we matched! Yes! After a few weeks of talking online, we decided to meet in person and go out for dinner and a movie. Tim thought our first date was a bust, but I thought it went fine. Two more weeks and a snow storm passed before our second date. Needless to say, the second date was a success and we have been having fun ever since!

how they asked

I had a conference trip scheduled in Chicago and invited Tim to travel with me. I had never been to Chicago and Tim jumped at the opportunity to serve as a tour guide. Since this was our first trip together, Tim planned a special day of sightseeing, brunch, and dinner. He made sure I packed a nice dress and heels (I am a runner and never wear heels) for our dinner. After I finished my conference activities and we are preparing for our day of sightseeing, Tim announces he has hired a photographer to take professional pictures of us. I did not think anything about it because we love taking candid photos together and professional pictures means we’re taking it up a notch.

On the day of our exploration of Chicago we got up, had brunch, went sightseeing and later prepared to take photos and dinner. Tim was a little anxious that day because it was cloudy and raining. He kept checking the weather report but I figured we would just take a few quick photos and then go eat.

When we finally made it to the photoshoot location, North Avenue Beach, we found our photographer, Peter, and he started to pose us. The first few poses were of us together. Just good, fun poses. I’m having a great time posing and laughing when Peter instructed me to turn around to get a photo of the Chicago skyline with my back turned away from them. I did not think anything of his instruction and turned around. After a few seconds, Peter tells me to turn around. When I turn around I see Tim on one knee and I lose it! I have no idea!


Proposal Ideas Chicago

Natalie and Tim's Engagement in Chicago

After jumping up and down and screaming I finally said YES! And Tim places the most beautiful ring on my finger! After a few tears and calls to my family, we continue our photoshoot! It started raining again, but I did not care!

Natalie's Proposal in Chicago

Once we captured the moment of surprise and pure joy, we called our parents and then continued with our photoshoot as an engaged couple! Yay!

Still riding on the wave of our engagement, Tim planned a nice dinner and arranged for us to have the best table in the restaurant with my favorite color flower on the table, champagne to toast our engagement and a wonderful dessert! Needless to say, Chicago has a new meaning for us and we are looking forward to spending many more trips and making memories in the Windy City!

Special Thanks

Peter Gubernat
 | Photographer
Trattoria 10
 | Restaurant