Autumn In-Home and Surprise Proposal Session | Jess + Bryan

Jess reached out to me about booking a shoot for her and Bryan’s dog, Mac. They had recently bought a house together, were planning out exciting nooks of their new space, and wanted a corner dedicated to their sweet pup. (I adore this idea!)

What she thought she was planning:

Jess’s idea was to get photos mostly of Mac and we would capture a few shots of the three of them together. Basically, part couples session, part “family” session with their Mac for her little corner of the house and for their Christmas cards this year. Cute, right? We would start off with some in-home photos of them in their Christmas onesies (!!!), change into cute autumn outfits, then have a more formal look for some nice photos for their home.

Meanwhile…

Bryan reached out to me separately telling me his plan to propose during our session together. But that’s not all…

What he was actually planning:

He was planning a full blown surprise proposal involving family and friends! Bryan had this awesome idea to get custom signs made that said “Jess, will you marry me?” on them (with sunflowers, her favorite, on them!) Check out Ashley and Ann here! He, our incredible planner friend Leshay, and I started a group chat to plan everything out in secret. Leshay titled Fantasy Football to keep Jess off the scent (lol). The plan was big and bold and had lots of potential bumps in the road (rain forecast, covid scare, you name it), and yet we were able to pull it off! It was a gigantic success!!

Oh and did I mention the seamless handoff of the ring? Bryan texted me mid-shoot that he put the ring in my backpack because it was obvious that it was in his pocket. Right as the couple rounded the corner and Jess saw the signs and their loved ones, Bryan led her by the hand, got into place, I grabbed the ring and passed it off to him, while still managing to click away at my shutter, and he got down on one knee! I am certain I nearly blacked out, but it truly couldn’t have worked out any better.

How we kept it a secret:

  • From my end as photographer, I let Jess lead. I always consulted her before “making any decisions,” and played the age-old comedy improv game of “Yes And.” We simply rolled with the punches and planned around her ideas.

  • While Jess was out of town one weekend, I went over to their house so Bryan and I could plan out all the logistics. We created a video to show how we’d come around the back of the house while all the family and friends waited in the front yard. Getting everyone to the front yard in the small window the couple and I were in the backyard with Mac was by far the most stressful part!

  • Fortunately for us, both sides of the family and all the friends were good at keeping the secret!

To Jess and Bryan:

Thank you from the bottom of my heart for placing your trust in me as your photographer and friend. It really means so much to me to have been involved in such a special day for you two. Bryan, you’re a rockstar at planning a KILLER surprise. I still cannot believe we pulled it off! Jess, thank you for thinking of me for your family photos. You two are wonderful people with such big hearts. Your love for each other is so evident and I cannot wait to continue the celebration as you plan your wedding and the rest of your life together. CHEERS!

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Dreamy Lafayette Square Fall Engagement Session | Natalie + Nick

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Grandparents + Grandchildren Family Session | Faust Park Family Session