45 blown-up mounted photos, about a dozen actors, a guitarist, waiters, a photographer, wine, hors d’oeuvres, champagne, roses, an engagement shoot, and a yes…

I flew into Chicago to meet Jenna on Thursday evening after she was invited to speak at a conference in New York and Chicago. On Friday morning, I started getting ready and told Jenna that I was going to try to look nice for the day. I was even going to blow dry my hair. Jenna emphatically told me she had no interest; after spending the week in conferences, wearing dresses, makeup, and doing her hair, she was set on going for a “relaxed” look. Ok…

At 2:00 on Friday afternoon we switched hotels and arrived at Hotel Lincoln, just in time for check in… or so Jenna thought. The concierge delicately tells us that our room is not ready yet. But, there is a photo exhibit on the rooftop lounge: the J. Parker. Luckily, Jenna doesn’t make a fuss and we make our way towards the elevator. In the elevator with another couple, we’re greeted by a host who tells us a little bit about the “artist”.

Ding… we arrive at the top. Jenna takes the lead and starts walking through the exhibit. A waiter comes by with some hors d’oeuvres– classy. The exhibit begins with photos in the Caribbean. Jenna seems to be flying through the exhibit! I need to slow her down. Waiters come by with some wine. “Josh – free wine! Grab one” – Jenna is excited.

Then come the photos of Europe. Lisbon is the first one Jenna recognizes – “That’s weird Josh. I used a similar photo in one of my syllabi.” Be cool Josh, be cool – “What city is that from again?” That was close… Moving right along. “And weren’t we there as well” – Jenna, pointing to a photo of Lima. “Doesn’t look familiar to me.” Disaster averted.

More snacks – sweet! A guitarist is playing in the background. We peruse photos of South America (our first back-packing trip together). These photos are quite distinctive. From the tiny city of Samaipata, to the floating island in Peru: “This is such a tourist trap, Josh. I literally have the same photo from our trip.” “Oh yeah, that does look familiar. Weird.” Apparently this is where Jenna sees the photographer not so subtly taking a photo of us, but she lets it slide.

Next come the photos from the American and Canadian cities. Jenna points to a photo and sarcastically says: “and I bet that’s the Ottawa tulip festival”. Yes, Jenna. It was.

We’re nearing the end of the exhibit and I knew she’d recognize the photos coming up. Boy, am I nervous… “Josh… that’s MY photo. THAT’S MY PHOTO! That’s Ronald McDonald at the McDonald’s Ajax clean-up day. And that’s my apartment in Waterloo. And that’s the Kawartha’s cottage”.

Believe it or not, she still has no idea what’s going on. Jenna’s thinking about data privacy, the cloud, wondering where she left her computer… and why someone would steal her photos and make an exhibit. She thinks, “These weren’t even my good photos!”

I grab her hand and pull her over to the corner of the rooftop lounge overlooking Lake Michigan and the Chicago skyline. Over my shoulder is a photo of Layla, on our condo balcony overlooking Toronto.

A light bulb immediately goes off in Jenna’s head – I could actually see it happen – Josh is proposing to me. These are my photos. They were not stolen. Holy shit.

Jenna laughs, cries, laughs some more. I nervously and excitedly spoke from the heart, reflected on our 6-years together, and promised to love her forever. I reach into my pocket, drop to one knee, and ask, “Jenna Leigh Jacobson, will you marry me?” She said YES!

After we catch our breath, take it all in, and call the fam, we freshened up (notice Jenna’s hair before and after) to explore the city with our amazing photographer, Chad Husar.

Thanks to Rachael Wilson, the incredible event planner, who helped me plan and set up the most spectacular proposal.