Kelsey and Justin

Engagement Proposal Ideas in IO Theater- Chicago, IL

How We Met

My fiance’s cousin, Brenden, was one of my good friends from college. Brenden invited me to a Halloween party back in 2016 that he and his cousin, Justin, hosted.

I had recently moved to Chicago, IL and was so excited to make new friends at this Halloween party. My best friend (now Matron of Honor) and I decided to go as “Cat-Dog” — yes we were attached all night! As we walked into the party, I thanked Brenden for inviting us and wanted to meet his cousin/roommate to thank him as well for hosting.

When Brenden introduced me to Justin, I immediately thought how cute he was! Brenden and Justin’s costume was a remake of a picture they took when they were young. It was hilarious!

Marriage Proposal Ideas in IO Theater- Chicago, IL

Justin wanted a picture of him and Brenden in their costumes. He so conveniently “misplaced” his phone. Justin had me take the picture and send it to him, so he very smoothly got my number.

Fast forward a few months and after many snap chats and random texts, we went on our first date with the same couple that sat at the table during our proposal at the improv theater. Our first date was a Chicago Bulls game, and it was evident that Justin and I not only had chemistry but were becoming best friends.

We continued to go on very special, romantic, thought out dates that Justin surprised me on each and every one. Within 2 weeks our relationship was already so full of love and within 11 months he asked me to spend the rest of our lives together!

How He Asked

Justin and I decided to take a big step and move in with each other. To celebrate the move, we decided to go out to a fancy dinner. In the middle of dinner, Justin asked if I wanted to meet some friends at the io Theatre in Chicago. I immediately said yes! Because we want there on our 3rd date and it was a blast. Little did I know what Justin had in store :)

Justin rented out the entire Chris Farley Theater at io Theater and added an additional improv showtime by “The Big Spoon” improv group. Justin and I showed up slightly late, and sat at the front table with friends who we were meeting there. Midway through the show, the improv group invited us up on stage for a special skit where they interviewed us about our relationship, which they then did an improv skit on. Following this skit, they added on a scene which was recreating the process of Justin planning the proposal starting with him asking my parents, all the way up to him calling the improv theater to book the venue, at which point I put it together what was happening.

They then invited Justin & I up on the stage that was filled with flowers and candles to set the mood. After I said yes, to my surprise the lights turned on to reveal the theater was filled with 70 of our closest family and friends. It truly was a fairytale proposal!

Proposal Ideas IO Theater- Chicago, IL

During all of the celebrating, Justin also surprised me with an “Engagement- Moon”, where we flew down to Naples, FL to his family’s condo for a romantic getaway the next day.

Our Video

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Special Thanks

Sirpilla Soirées
Planning
Io Theatre
Planning