Kevin & Jenna | Kevin's Proposal | Chicago, IL Proposal Photographer

Kevin called me in near-panic early on a Thursday morning. He was planning to propose to his girlfriend, Jenna, in less than 48 hours and the photographer he hired had stopped responding to calls, texts and emails. Luckily, I wasn't booked the next day and love shooting proposals.

Within the first few minutes I could tell this was going to be a fun shoot. Kevin wanted to have a bunch of pictures representing their relationship along a wall by the Chicago River. He was excited about it, I was excited about it and so we set our location, planned out the timing and where they would enter from and then waited to execute.

The next day, I stopped at the store to pick up a big box of pictures to post along the riverwalk. I showed up near the location, parked and texted Kevin to let him know I was walking to the River. I was way earlier than I needed to be but it was a little cold that day and I had a feeling the pictures would have trouble sticking. As it turns out, the cold wasn't the problem, but the wind was.

When I got down to the riverwalk, I realized that all the sets of stairs looked the same. After analyzing the reference pictures Kevin sent me with the same eye I use for finding Waldo, I noticed a building in the background. It wasn't much, but it was enough for me to figure out which wall to put the pictures on.

As I said, it was cold and windy, so the riverwalk was pretty empty. I started taping the pictures to the wall and people started to notice. A man and his daughter stopped by to ask what I was doing, teared up a little when I told them, then wished me luck and left. Two women approached me a few minutes later, after seeing me scrambling around the riverwalk picking up the pictures that were blown off the wall. Again I told them about the proposal and they thought it was adorable (then took a selfie with me for Snapchat and went on their way). At this point I was surprised everyone had been so positive about the guy taping pictures to a wall in front of Trump Tower. As I finished taping the pictures to the wall and double checked that they weren't going to blow away the second I turn around, I notice an older lady standing maybe 10 feet behind, silently watching. I smiled and went back to what I was doing. Less than a minute later, she walks over. I expected her to ask what the pictures were and why I had camera gear, like everyone else had. WRONG. Rapid fire she said:

What are you doing?
Who gave you permission to do that?
You don't have permission to do that.
This is vandalism. You can't destroy public property like that.
I'm calling the police.

Before I could respond, she took her phone out, and stormed off, likely calling the police. Well, this wouldn't have been the first time someone has called the police on me for doing my job and it probably wouldn't be the last. I continued with what I was doing and within maybe 5 minutes, 6 security guards approach me.

Security: What are you doing?
Me: I'm a photographer. My client is going to propose to his girlfriend in a few minutes and the pictures are of the couple.
Security: How long are you leaving it up?
Me: He should be here in about 30 minutes, he'll propose, then I'll take the pictures down. Probably in less than an hour.
Security: Oh okay do your thing then!
Me: :)

It's nice when things go smoothly.

Security walked away, but found a spot nearby to watch the proposal. I found a great spot to hide near the underpass. There was no way they'd see me but I had a great vantage point. Kevin and Jenna came down the steps shortly after. From here, the pictures can tell the story better than my words (and that's what you came here for anyway, right?)...


Of course, she said "yes."