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Jenna and Don’s Engagement Session at Olive Park

Jenna and Don’s Olive Park engagement session was an absolute joy! Their happiness is simply contagious. Walking through this hidden gem with them felt like a dream. They’re so in love and sweet together, and capturing their love story in photos was truly a pleasure.

Olive Park Engagement Session at Sunset

Olive Park, with its mix of natural beauty and the city skyline by Lake Michigan, was the perfect spot for our shoot. Walking through the park, Jenna and Don were constantly holding hands, sharing kisses, and laughing. Their neutral outfits and the soft light were just right for the look we were going for. But the real magic kicked in when the sun set, giving their photos a warm, romantic glow with the city in the background. We took full advantage of the golden hour to capture that dreamy vibe.

The Proposal

Now you’ve got to hear how these two got engaged! It’s such a good story! They had plans to visit the Zoo Lights at Lincoln Park Zoo with a couple of friends one evening. While getting ready, Don was acting a bit odd, but since they were leaving for a big vacation in two days, Jenna thought he was just excited. She had a hunch something was up, but when their friends texted about the rainy weather and suggested canceling, Jenna brushed it off as paranoia.

Once they got to the zoo, everyone was walking quickly and not really looking at the lights, which Jenna found strange but didn’t dwell on. When they reached the tunnel of lights, Don got down on one knee! Turns out their friends were in on it all along and had sent that text to throw her off. They celebrated at a wine bar where “The Wedding March” played over the speakers. Jenna kept wanting to call her parents, but everyone told her to wait until dinner. Later, at Cafe Ba Ba Reeba, she expected it to be just the four of them, but Don had planned a whole celebration with friends, his family, and her parents in a private room! She was totally surprised! They ended the night with Malört shots at a bar across the street. It was incredible!

Knowing They Were “The One” for Each Other

When I asked the couple to share how they knew that they were “the one” for each other, they gave the sweetest answers. Don knew Jenna was the one when even mundane tasks like grocery shopping were fun. About a month into dating, Jenna went away, and Don was so sad when he dropped her off at the airport that he cried. Jenna realized Don was the one because they could talk endlessly and still have so much to talk about. She still gets excited to see him, even if it’s just when he comes back from walking the dog!

Olive Park: Skyline Views Meets Natural Beauty

Afterward, we headed to Ohio Street Beach, which offered stunning views of the city skyline. I love how the combination of the water’s natural beauty and the urban feel of the tall buildings turned out in the photos. Jenna and Don’s Olive Park engagement session was the perfect spot to document this exciting moment in their lives.

The next year will be full of planning and preparations for all the stunning details of their wedding at The Drake in Chicago.

Jenna and Don, thank you so much for having me photograph and document this beautiful season in your love story. You two are such a joy, and I had so much fun exploring Olive Park with you! I’m so excited for you both and all the adventures that lie ahead! Enjoy every minute of being fiancés! Sending the biggest hug and all my love! xoxo


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