When Tommy messaged me to ask if I was available for a trip to Chicago so I could capture his proposal to Ari, I couldn’t say no.

I already knew the two, I had photographed them twice in Chicago and they were even so nice to offer me a place to sleep the very first time I visited the windy city. Check out our first session together. This time was even more special to me. So I rented a car, and made the drive down to Chicago. I didn’t even post online about the trip since Ari and I follow each other and I wanted it to be a total surprise.

Tommy did a great job with Plan A and “Plan B in case the weather is trash.” Luckily it was a beautiful, warm day so Plan A was on. I was in a group chat with Tommy and some family who would hide nearby with champagne ready after he asked the question and she said yes. He shared his location so seeing him and Ari had just left their apartment and were about 20 minutes away I captured some family photos and staged the group nearby where they could watch this all happen yet be just out of sight. I threw my hair up in a bun, knowing Ari may recognized me with it down then went full on ninja mode behind the trees so I wouldn’t be discovered as they walked past me and to the spot.

chicago Proposal photogrpaher

When they sat on an edge overlooking Lake Michigan Tommy pulled the ring out and had it behind his back as a signal.

He then said some things to Ari, stood up, then got down on one knee. She said “yes,” and didn’t even see me until Tommy pointed me out. Then to add to the excitement, I waved the family over. At this point Ari is in happy tears while everyone is exchanging hugs, congratulating Ari and Tommy, wowing over the ring, then confessing all the secrets they kept and white lies they told Ari so this day would stay a surprise.