There’s something so magical about a well-planned surprise proposal. The suspense, the joy, the emotions—it’s a moment that lives in your heart forever. And when you add in a jaw-droppingly gorgeous setting like the Chicago Botanic Gardens and a reaction that makes everyone reach for the tissues? Well, you’ve just created a memory for the ages.

Take Anya and Jarrett’s recent surprise proposal as a perfect example. I’ve been lucky enough to document their incredible love story from this unforgettable moment all the way to their wedding day, and I’m still thinking about how beautifully it all began. If you’re dreaming of pulling off your own perfect surprise proposal, let me walk you through some tips (and gush about this dreamy proposal while we’re at it).

How to Plan the Perfect Surprise Proposal in Chicago (or anywhere!)

Step 1: Pick the Perfect Location

A great proposal starts with a meaningful location. The setting should feel special and intentional, whether it’s where you had your first date, a place they’ve always wanted to visit, or simply somewhere breathtaking.

For Jarrett, the Chicago Botanic Gardens was the spot. It’s a true slice of paradise, with lush greenery, dreamy blooms, and serene water views—basically, the kind of place where romance is in the air. And it turned out to be the ideal backdrop for this life-changing moment.

Step 2: Timing is Everything

Here’s the thing about proposals: timing really matters. Whether it’s ensuring the lighting is just right (hello, golden hour) or dodging a potential rainstorm, a little flexibility and planning go a long way.

In Jarrett and Anya’s case, the weather had other plans. It had been raining on and off all day, and we were all holding our breath, hoping the skies would clear. And guess what? The rain stopped literally minutes before the big moment. (Talk about fate, right?) Sometimes, you just have to trust that everything will fall into place.

Step 3: Make It Personal

Adding personal touches to your proposal makes it even more meaningful. For Jarrett, this meant organizing a surprise post-proposal party with their closest friends and family—and yes, their precious fluffball of a puppy, Murphy, was part of the celebration, too! It was such a thoughtful detail that showed just how much care he put into making the day unforgettable for Anya.

Shoutout to Jarrett for absolutely nailing it here. Not only did he pick the perfect spot, but he also thought ahead to seamlessly combine the surprise proposal with the joy of celebrating with loved ones. (Take notes, people!)

Step 4: Capture the Moment

This might just be the most critical step: hire a photographer who knows how to stay incognito until the perfect moment. (That’s where I come in!) I can’t tell you how much I love documenting proposals, especially when the reaction is as priceless as Anya’s. Cue the tears, the laughter, and that look of pure joy—those are the moments you’ll want to remember forever.

After she answered with an excited and happy-teared “Yes!” (of course!), we spent some time wandering through the ss for some post-proposal photos. And let me tell you, they were sublimely happy. The love, the smiles, the giddy excitement—it was all there, and it was everything.

Step 5: Celebrate in Style

The surprise didn’t stop at the botanic gardens! Jarrett had arranged a celebration at a nearby restaurant, where their family and friends were waiting to congratulate them. The room was filled with happy tears, hugs, and so much love. And Murphy, their adorable pup, was the cherry on top of an already perfect day.

Pro-tip: If you’re planning a surprise party, give your guests a heads-up about timing and location so everything runs smoothly. Also, bonus points for including your furry family members—they always steal the show (in the cutest way)!

Step 6: Soak It All In  

 Amidst all the planning, excitement, and happy chaos, don’t forget to pause and savor the moment. Proposals can feel like a whirlwind, but those fleeting seconds of pure love and connection are what it’s all about. After all, this is the beginning of one of the most beautiful chapters of your life together.

Jarrett and Anya’s day was filled with many of those magical, soak-it-all-in moments. Every second felt intentional and meaningful, from the quiet anticipation leading up to the proposal to the heartfelt toasts at their celebration. And can we just take a moment to acknowledge how perfectly their love story unfolded that day? It was a reminder that when you lead with love and thoughtful effort, everything seems to work out beautifully—even if a few raindrops try to make an appearance.

Why This Proposal Will Always Be a Favorite

I’ve photographed a lot of love stories, but there’s something so special about following a couple from their proposal to their wedding day. Since that magical evening at the Chicago Botanic Gardens, I’ve gotten to know Anya and Jarrett even more through their engagement session, boudoir session, and wedding celebrations in Milwaukee. (Spoiler alert: They’re seriously the sweetest couple ever.)

Every time I look back at their proposal photos, I’m reminded of how much thought, care, and love went into that moment. It’s a testament to how deeply Jarrett loves Anya and just how perfect they are for each other.

Planning Your Perfect Surprise Proposal (or Dropping a Hint)?

So, if you’re planning a proposal, remember this: it doesn’t have to be extravagant to be extraordinary. What matters most is that it reflects who you are as a couple and the love you share. Keep it personal, stay in the moment, and don’t be afraid to let your emotions shine. Because at the end of the day, it’s those real, raw, heart-stoppingly beautiful moments that make it unforgettable.

And if you need someone to help you capture it all? You know where to find me—I’d be honored to document your love story, tears, laughter, and everything in between. Here’s to all the “Yes!” moments still to come! ✨

Want more proposals? This way, please!