Talk about the perfect summer night for a Chicago engagement session! I had an absolute BLAST photographing Izzy + Jack while we ventured around the Winnemac Park and Montrose Beach.

Naturally, I asked them about the story surrounding the proposal. Both gave me a different answers, which was super cool!

Jack’s Side of the Story

“In 2021, I planned on visiting my hometown of St. Louis with the primary goal of retrieving my mother’s wedding ring,” Jack said. “My brother had been holding onto it ever since she passed in 2018. Isabelle thought we were just visiting family and my Aunt’s new puppy (which was also quite important). During a lunch meetup, my brother slid me the ring while Isabelle excused herself for a moment.

While we had already discussed our futures and marriage together I still wanted to make the actual gesture a surprise. The original plan was to take her on a nice dinner date to a local restaurant’s patio and pop the question on the way back home through the park near our apartment, ideally during a sunset. Mother Nature was not too kind and a storm rolled through, canceling the dinner. (No indoor dining for us during peak Covid, unfortunately). We opted to grab some extremely mid pizza and headed home to watch TV — not ideal. So I waited…”

The Proposal

“With the ring weighing HEAVY in my pocket, I then opted for Plan B. Now that it was close to the date of our anniversary, I suggested we have a charcuterie picnic at the park on a nice sunny day and decided to propose at the park and enjoy each other’s company. But of course an interesting twist appeared! Our mutual friends who happen to live across the park texted asking us to meet up at the park with them right as we were about to leave. Isabelle quickly texted back and agreed while I was secretly sweating and texted our friends separately to wait about half an hour before coming because I was going to propose 😉. So we took our food and dog, Nora, over to the park and set up.

As Isabelle had her back turned while setting up the blanket and I was getting extremely nervous, I got on one knee with the ring and asked her to marry me. She said “yes!” We ended up not eating a single bite of the food because Nora was more interested in it than we were. Eventually our friends joined us to celebrate with us!”

Izzy’s Side of the Story

“In 2021, the year that would be our seventh anniversary, Jack and I decided that we’d be engaged by the end of the year,” Izzy said. “Against my typical type-A nature, I asked Jack to surprise me with the proposal (which is an impossible task, because I’m super nosy!). By the time our anniversary rolled around in September, I was getting a little impatient. But, because I hadn’t really noticed him planning anything, I definitely still had blinders on. When Jack suggested a fancy Friday courtyard dinner for our anniversary, I didn’t even think twice. He did keep emphasizing a walk through Winnemac, either while we were waiting for the table or afterward, which I thought was weird…”

The Proposal

“Jack had to chaperone homecoming on Saturday (he’s a high school physics teacher), so he suggested that on Sunday morning we go have a little picnic in Winnemac Park. He picked up fancy charcuterie, some canned wine and we got dolled up, which also should have been another hint to me. But in my defense our anniversary was a very good cover! Jack was kind of being quieter than usual the whole weekend, but I thought it was because he was a little bummed out about his Plan A getting rained out.

We got to the park and set things up, but then our dog Nora went bananas for the salami so we had to put everything away. Jack was saying cute, lovey things to me — which is not a rare occurrence (brag) — and I literally had my back to him and my sunglasses on, just *vibing* in the sun. I didn’t realize he was proposing until he was pulling out the ring box! And then I fully screamed, “WHAT!” out loud and probably scared some nice people. And duh, I said yes.

The best part was obviously the proposal, but the second best part was that I had accepted an invite from our best couple friends to meet up in the park that afternoon — because I was that much not onto Jack’s schemes — so they got to come celebrate with us right after, which was so special since both of our families are several states away. And Nora ate a bunch of grass, the end.”

Chicago Engagement Session

My side of the story, you ask? Well, I got to photograph their epic Chicago engagement session in Winnemac Park. We eventually made our way over to Montrose Beach for the sunset. The evening was amazing and I got to meet the incredible Nora. She is the goodest girl. I can’t wait for Izzy + Jack’s wedding next spring! :)