Millenium Park Proposal in Chicago

How we met: Jason and I met in 2008 at Jason’s Halloween party in college at Northern Illinois University. Jason knew dressing up as a Teletubbie would be a tough sell, but I couldn’t overcome his charm. We started dating in November 2008 and the rest is our fairy tale.

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how they asked: Jason had a photographer who we previously worked with in a past photo shoot to setup another shoot. I thought that it would be another couple’s shoot and didn’t suspect anything of it. However, Jason had other plans.


The photographer told me to face the opposite direction where I was immediately confused. When I turned around and saw that he was on one knee, I was completely surprised! When I realized what was happening, my heart was immediately filled with joy and said “YES! Of course!

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From his perspective: I knew I had her fooled when she didn’t question one thing. The photographer positioned Cassie to have her back towards me and I looked at him to confirm that he was ready. Then I pulled out the ring, and as sweat dripped down my forehead I muttered the words, “Will you marry me?” Perfect timing with her twist and when her face went from confusion to shock, I knew the hard part was over.


Photos by Peter Gubernat Photography