jon & jess: surprise proposal in chicago

engagement photography

Oh friends, I’m so excited to share these photos with you! If you recall from my weekend wrap up two weeks ago, I eluded that I couldn’t mention the main reason we went to Chicago for a quick trip. But now, I can shout it from the rooftops: we were there to photograph a surprise proposal! And not just any surprise proposal, but a proposal for two of our sweet friends. Jon is my husband’s best friend and was the best man in our wedding– so when he told us in secret that he was going to be proposing to Jessica soon and that he wanted me to capture it, I was honored! (You may recognize these two from their Chicago couples’ session last fall.)

So we set our planning into motion and came up with numerous ways to do a sneak attack for photos- but ultimately realized we weren’t going to risk it. We told Jessica that Jason was coming up for the Shamrock Shuffle (side note: that wasn’t a lie, he really did run it!) and that if we could find someone to watch our animals, I would probably come along. (That part was definitely a lie– sorry, Jess!) On Saturday, Jason and I got up early and made the drive to Chicago. The plan was that they were going to meet us near Navy Pier to go to brunch. But we knew that springtime in April in Chicago would be risky with lots of people, so we picked Olive Park to be *the* location because of its awesome view of the Chicago skyline.

Jon & Jess arrived around noon to the park and Jason and I pretended we were just exploring the park (which we did, by the way!) but honestly, it was all for location scouting. Since we arrived about 45 minutes before they got there, I scoped out where I wanted to shoot and crossed my fingers that everything would go as planned. And so, they arrived and I casually asked Jon to take a picture of Jason and I. After that, I said “oh, let me get your picture too since we’re here!” So we took one and then I went towards them and fixed Jessica’s scarf (it was fine, but that was the cue to Jon that I was ready and it was go time!) I walk back and got into position and had them stand hand in hand but a few feet apart. And that’s when the magic happened— she said yes!

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Don’t get me wrong, catching the proposal itself was incredible– but my favorite moments are right after when there’s so much happiness and joy!

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Congratulations, Jon & Jess! We are so excited for you. Thank you so much for allowing me to capture this special moment in your life!

  1. Sharon says:

    Beautiful pictures for this lovely couple. COngrats Jae’s and Jon!

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