Jason and Lilli - LakeFront Surprise Proposal

July 10th 2017

Jason and I were previous colleagues from a few years back and we had not seen each other for a long time.  However, after seeing some of my work on Instagram he reached out asking if I would help capture his surprise proposal to his girlfriend, Lilli, so of course I said yes. 

He texted me a week in advance asking if I would do it, and then we started game planning on the time and location.  He went a couple of days before to scope out the spot and then dropped me a pin for the exact location at the Shedd Aquarium on the Lakefront Trail.  Since Chicago summers draw people out of hibernation, he was worried there would be too much foot traffic.  Luckily, when the time was right he only had to dodge a couple of bike carriages and got a moment of privacy.  

If anyone knows Jason he has a big personality and great salesmanship, so coming up with a diversion was not a problem.  He told Lilli he had a friend in town and they were going to eat dinner with his friend and their parents at Mastro's, but wanted to take a quick stroll on the lakefront first.   I got there about an hour before to make sure I was in position and wouldn't miss anything once it was time.  Upon their arrival, they walked down to the Lakefront Trail, walking past me as I was waiting for them and of course Jason played it cool.  I slowly trailed behind them making sure I was ready, and then just as they were coming around the bend of the aquarium he got on a knee and went for it.  She was completely surprised, and of course said yes!

Congrats you two!