How to Plan a Proposal and Pop the Question

Written and Photography by Kate Scott Photography

Tis the season for getting engaged! 

As a Chicago wedding photographer, I’ve photographed dozens of proposals over the years. And here’s a secret: each proposal is completely unique! The holidays are one of the busiest times of the year for couples getting down on one knee and popping the big question. There are so many truly great locations in Chicago and the suburbs to plan a proposal; it just requires a little bit of planning. When I’m asked to capture a proposal, I’m always excited! It is one of the few truly candid moments that can never be recreated, so it’s important to make sure you have everything planned and booked ahead of time. Here are some of my tips for ensuring your proposal goes off without a hitch!

Know Your Audience

Your relationship with your partner is completely unique, which means your proposal should feel just as special. If your partner is more introverted or shy, there are plenty of public places where you can pop the question that are intimate and quiet. One of my favorite locations in Chicago is the Garfield Park Conservatory; there are so many hidden, plant-filled corners, and it’s warm year round. Plus, a photographer in a conservatory doesn’t raise any suspicions! And don’t worry-I am an expert at being stealthy.

If your partner wants a more city centric view without feeling too cliche, the skyline at Milton Lee Olive Park in Chicago is absolutely perfect. Stationed next to Navy Pier and across the lake from the Mag Mile, the views are classic and somewhat unique. Plus, there isn’t nearly as much foot traffic as somewhere like Millennium Park.

The most important thing to remember is that this is a moment you will both remember forever. Take your time picking the right place and planning the moment. If you want to propose at the bar where you had your first date, or in front of your favorite hot dog stand, we can make that happen! 

Plan Ahead

Once you’ve picked your dream spot, it’s time to make sure all of your ducks are in a row. Many public places require a photography permit, including both the Garfield Park and Lincoln Park Conservatories, as well as the Morton Arboretum in Lisle and the Chicago Botanic Garden in Glencoe. Most times, you simply need to apply for a permit and pay a license fee beforehand. You can always check the location’s website for more information.

If you are planning on proposing in a more intimate location such as a restaurant or bar, email the venue beforehand to make sure they’re okay with it. Some places, such as London House, will not allow any photography without prior approval. Plus, if you mention you’re getting engaged, they might surprise you with some champagne or dessert!

Another important factor to remember is time of day. If you are planning to propose at night in an outdoor space, the lighting may not be ideal. I try not to use flash during the proposal itself, as it’s a huge distraction for the couple in the moment. We can always use flash afterwards, though! Golden hour (the time just before sunset)  is a perfect time to propose if you’re doing so outdoors. During the winter, golden hour can add an amazing feeling of warmth to an otherwise chilly moment.

Remember to Breathe!

Popping the question is a once in a lifetime moment! It’s okay to be nervous; in fact, nervous energy can make for the most sincere and joyful photos. You don’t have to write out a huge speech or spend a ton of money to create the perfect memory for your partner. Just remember that you’re proposing for a reason; the love that you share with each other is completely unique, unmatched, and worth more than a thousand words. It’s my job to make sure the moment is captured perfectly, and I promise that every second of anxiety and planning leading up to the proposal will be worth it.

If you are interested in booking Kate Scott Photography for your upcoming proposal or other photography work, please reach out to her directly via her website or her CHI thee WED storefront!