Courtney and Brent

How We Met

Brent and I met in high school and only knew of each other from walking the halls and a few mutual friends. Senior year prom was around the corner; we both needed dates. Barely knowing him and his desire and efforts to make everything he does perfect, he asked me to prom in the best way possible. After leaving the school gym for a few minutes during cheerleading tryouts, I walked back into an audience of about a hundred girls cheering me on, and my teammates in stunts holding signs that said, “PROM?”

Engagement Proposal Ideas in Chicago, Illinois

Prom night was nothing short of amazing! We celebrated post-prom the next day/night with some friends in Gelena, IL. That summer we officially started dating and tried to hold time still knowing we were off to different universities in different states in a few months. Since then, Brent and I graduated college and became adults. Brent started filming wedding videos for friends of ours on the side and I help with video ideas and planning. Now it’s our turn to start the planning and we often find ourselves asking, “Who is going to film our wedding??”

Where to Propose in Chicago, Illinois

how they asked

Brent surprised me with a weekend trip to Chicago to explore the city as a Valentine’s Day gift. He planned for us to stay at the W Chicago-Lakeshore where he said had an amazing view of the lake. Friday night, we got dinner with friends of ours and stopped in a few different bars.

Marriage Proposal Ideas in Chicago, Illinois

Saturday morning, he told me he wanted to film some scenery for the next video he was editing. He is a photographer and videographer, so I am used to him filming me on every trip we go on. He took me to the skyline view in front of the Adler Planetarium and told me to face the skyline so he could film me which was a norm for him to have me do. Out of the corner of my eye, I noticed him walking towards me, standing on one knee with tears in his eyes, asking me to spend the rest of my life with him. I immediately came to tears knowing that I finally get to call my best friend my fiance.

We finished our weekend celebration with champagne, ice skating, and dinner. This weekend was all I could ever ask for: touring the city and getting engaged to the love of my life. Definitely a weekend I will never forget and will never get tired of talking about. Forever grateful to have met Brent and to have shared so many wonderful memories with him growing up and becoming the people we are today.

Our Video

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Special Thanks

Brent Thorne
Brent Thorne