Jessica Brees

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Hey friend!

I'm Jessica: wife, mom, photographer, educator

I'm a creative girl boss, obsessed with wedding photography and videography. I have a degree in education and want to bring that into the creative industry by teaching other bosses how to make their dreams come true! When I'm not working, my days are filled with long walks down every aisle of Target while sipping my Pink Drink and listening to my newest playlist. It's the small things!

April 5, 2019

High School Sweetheart Lake Como Surprise Proposal



Today is the day I’ve been waiting for for almost ten months! I can finally let you in on one of the biggest secrets I’ve ever had to keep: a surprise proposal on the boardwalk of Lake Como!

Kyle and I started messaging secretly on Facebook so long ago, planning every detail of his proposal. It was originally planned to be in Paris, with the Eiffel Tower as the backdrop, but recent rioting in France changed the trip to Milan, Italy. I spent hours on Pinterest learning location ideas and shooting tips for the area. We finally landed on the Lake Como area and planned the entire day trip over a Skype call less than a week before Kyle and Alison left for Europe!

It was on her birthday, nonetheless!

As if I wasn’t feeling the pressure of this huge, milestone moment already, Kyle reminded me that he was proposing on Alison’s birthday! Can it get any dreamier than this? A proposal, on her birthday, in ITALY? I was freaking out inside, so I can’t imagine how Kyle felt in the days leading up to the big moment.

Jason and I arrived in Italy on Thursday and drove to Lake Como to scope out the spots and send Kyle more secret messages about what time he would be there, and where we would stand in relation to where he would stand. This is much more difficult than I imagined, trust me! It’s a lot of little details to line up. Next thing we knew it was mid day on Friday and I was in full blown panic mode! I chatted a mile a minute to Jason, trying to make sure I didn’t forget a single thing: did I have my hat and sunglasses, do you think she would notice me, did I bring the second camera body, did all my messages go through to Kyle? My brain was a mess with this high-stakes moment! Months of plotting, planning, and preparation rested on just a handful a seconds and a few clicks of the shutter.

We were fluttering nervously and thinking a mile a minute, but we almost forgot where we needed to be! We stopped, gave each other a high five and a kiss, snuck in a quick selfie, and split up to get ready. I tracked Kyle’s location on my iPhone making sure we didn’t miss him. My heart was pounding so hard as they inched closer and closer on the screen.

So we waited.

The seconds felt like minutes. The minutes, hours.

We had to remind ourselves to breathe.

Their once-in-a-lifetime moment. Our once-in-a-lifetime moment.

Was just a moment away.

I kept thinking, please give me sharp focus… solid composition… and the right—

“That’s them!” I thought.

And the rest, as they say, is history.

This is literally how close I was to them and she never noticed I was there shooting!! (I’m the one in the baseball cap creeping by the Aladdin Carousel! 🤣)

This was the coolest moment in my photography career so far! I dare anyone to try and top it…I’m game! 😉

Once the proposal was over {and she so happily said yes} Kyle let Alison know that I was there too and I literally RAN over to give her a huge hug! This was a moment I tried to plan out in my head as well, but I was so excited for them that I lost all professional composure and just jumped up and down and stumbled over my words instead! Try Breezy style, right there!

After we all had lunch together we wandered the streets of Como and took some “post-proposal photos!”

Since Alison follows along with my  social media, one of the biggest keys to pulling off the surprise was to make NO mention of us traveling to Europe. No Instagram posts. No stories. No hints. Nothing. THIS WAS SO HARD! But I am proud to say that I pulled off the surprise of my lifetime, and Kyle pulled off the surprise of his as well! I will be sharing their actual “engagement” session later this week, but wanted to leave you with a fun behind the scenes photo of our Skype with Kyle…when the reality of what was about to go down hit him!

If you think you want to plan a destination proposal, I am SO the photographer for you! Let’s do some secret chatting and plan it out! 🤫💍

If you enjoyed this blog post, you may also like some of these!
A Glowy Winter Engagement Session in Sioux City, Iowa 
A Destination Winery Wedding in Round Lake, Minnesota

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