The Perfect Chicago Skyline Proposal


November 27, 2022

It was a chilly day in the city when we did Nick & Kaitlyn’s proposal session, but the sun made the whole day feel glowy, and warm, and gorgeous. Nick messaged me about a month before he planned on proposing to Kaitlyn, so I was so glad that I had the date available. He told me that he wanted me to photograph the proposal because Kaitlyn had mentioned that she would love it if I could photograph their wedding someday. (Major rockstar fiancé points for filing that hint away.) We watched the weather all week but waited until the day before Proposal Day to see if the October weather was going to be on our side. Nick had a few spots picked out and told me that the Chicago skyline was so important to him. I mentioned Olive Park and its beautiful pier and after scouting it, Nick was sold. 

Everything was falling into place and the pier was totally empty by the time Nick walked Kaitlyn over to the spot we picked. I had to get creative and wrangle a few strangers to act like they were talking to me so I could keep my back to Nick and Kaitlyn! They were the best and kept an eye on my couple so I could turn around and start capturing at exactly the right moment. I melted at the way Kaitlyn’s face lit up when Nick dropped to his knee. Her surprised look at seeing I was photographing the moment made my entire weekend! Nick did an incredible job surprising Kaitlyn and I was so truly honored to have been there!

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