Kelsey and Justin

Wedding Proposal Ideas in io Theater, Chicago, IL

How We Met

Justin & Kelsey started dating in January 2017 and it quickly became evident that they were a match made in heaven. After a couple months of dating, Justin asked Kelsey to be his plus one at his mother’s wedding and invited Kelsey on his work incentives

trip to Alaska which would take place during summer 2017.

Justin decided that he was going to propose to Kelsey during October 2017. After receiving Kelsey’s parent’s permission to propose, he thought of the perfect proposal idea, getting Kelsey the mini goldendoodle that they’ve dreamed about for months! After their landlord shot that idea down, Justin had to scramble to think of the perfect, swoon worthy proposal.

Marriage Proposal Ideas in io Theater, Chicago, IL

Where to Propose in io Theater, Chicago, IL

Kelsey's Proposal in io Theater, Chicago, IL

Kelsey and Justin's Engagement in io Theater, Chicago, IL

How He Asked

The proposal: Justin rented out the Chris Farley Theater at io Theater and added an additional improv showtime by “The Big Spoon” improv group. Justin and Kelsey showed up slightly late, and sat at the front table with friends who they were meeting there. Midway through the show, the improv group invited Justin & Kelsey up on stage for a special skit where they interviewed them about their 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 her parents, all the way up to him calling the improv theater to book the venue, at which point Kelsey put it together what was happening. They then invited Justin & Kelsey up on stage filled with flowers and candles to set the mood. After she said yes, to her surprise the lights turned on to reveal the theater was filled with 70 of their closest family and friends. Following the celebrations at io Theater, we went to Frosty’s Christmas Bar to continue the celebration with all of their family & friends!

***My name is Nicole Sirpilla, I helped Justin plan & execute this proposal and am submitting this on their behalf. I have already been granted their permission. ***

Our Video

Watch more proposal videos & follow @HowHeAsked on Instagram for more stories!

Special Thanks

Marie Dillon (Mother of Kelsey) | 
Photographer