Let me just start by saying, Jeryn and Drew are the SWEETEST couple, and I am so happy Drew reached out so I could capture their proposal at Chicago’s beautiful lakefront.

A little bit on their story

“Drew and I met at our apartment complex! You could say it was love at first sight I lived on the second floor and he lived below me on the first floor. I remember it was during the week because he was on his lunch break, but I was taking my dog out and ran into him in the hallway lol.”

“We exchanged pleasantries and went about our days. I came home from work that night and he had left a cute little note at my door asking for my number and how to use our laundry services I’ll give him credit where credit is due because he’s definitely made a lot of the first moves! After the note he would ask me to go on dog walks all the time, made me dinner, would have movie nights, and asked me to be his girlfriend. And to move in with him! He’s pretty much done it all lol.”

“Everything between Drew and I has happened fast, but I think when we met, we both knew this was it for us.”

The Proposal

This was actually their first time visiting Chicago, they are from Kansas, so they not only got to have such a beautiful experience in Chicago but they also got to come home from their trip engaged!

Proposals are SO MUCH FUN to capture, between the planning, coordinating, blending in with the crowd, there can be quite a bit that goes into the planning of a proposal.  If you’re planning your own proposal in Chicago and plan to have it captured, here are some things you will want to think about as you’re planning your surprise proposal!

1. Location

If you plan to have your proposal documented by a photographer, you’re going to want to choose a location where I can blend in.  Public places in nature, or busier streets are perfect locations to plan your surprise proposal.  

For Drew and Jeryn’s proposal they got engaged at Milton Lee Olive Park next to Ohio St. Beach and I pretended to be a tourist!  I wandered around capturing the skyline, this is a pretty easy one to pull off for a lakefront proposal since there’s such a gorgeous view of Chicago in the background. It makes it very believable!

2. Time of Day

The best time of day lighting wise will be around golden hour for your photos.  If you plan your proposal a little over an hour before sunset or right at sunrise, you’ll be able to have about an hour of time for photos after you propose before the lighting becomes a little more difficult.  The two of you can bask in your soon to be wedded happiness and we can run around to take some beautiful photos for your save the dates!

3. Having a backup plan

With everything being a surprise, and us living in the city of Chicago, you have to be ready for anything, ESPECIALLY when it comes to a surprise proposal.  I will brief you with what I am wearing, and hang around in your general vicinity but you’ll have to make the ultimate call on where to drop down on one knee.

For Jeryn and Drew, there were multiple wedding parties where we originally planned to do it, so I quickly texted Drew and let him know to keep walking past the triangle and to just stop whenever he felt like it as long as there was a good view of the skyline. Luckily the lakefront has plenty of amazing views of Chicago, so getting the skyline in the background of their proposal wasn’t hard to do!

4. Have a cue! 

One of my favorites is suggesting that you take a selfie or make a TikTok.  Prop your phone up against something and then take a few steps away from the phone and then get down on one knee!  That way you can take a video and I will know when we are ready to go!  Then if you can, try to stay down on your knee until the ring is on your partner’s finger.  

Jeryn was standing by the ledge as Drew was propping his phone on the ground, using Jeryn’s bag as a phone stand, thinking that they were taking a selfie (he actually had her family and some close friends on facetime to witness the moment). Drew walked to Jeryn, pretended to take a few photos, and well… went down on one knee and asked her to marry him.

5. Be in the Moment

Then last but not least, remember as you’re heading into this big moment for the two of you to be there in the moment and do what comes naturally.  Things never go quite as planned, ultimately you’ll want to just do your best to be present in the moment and do what feels right for the two of you.

It’s funny because when were were taking photos, Drew said, “She didn’t even let me say my speech, and just said yes” lol. He got to say his speech when I had them go by the edge of the triangle, by the railing, and told them to say “why they love each other”.

I’m so glad that Drew reached out to me to be a part of his and Jeryn’s lakefront proposal, getting to share this moment with them and be a part of their first experience in Chicago was truly special! Looking for some more sweet engagement stories like Drew and Jeryn’s? Check out the engagements tab of my blog!

For other proposal stories, check out:

Adler Planetarium Proposal

Proposal at the Chicago Botanical Gardens

Book a photographer to capture your proposal story!