Photographing my sister’s surprise engagement last April was only the second time I had done this for a couple, but each time has been filled with excitement! My mom had given me a heads-up that my sister’s boyfriend, Max, was planning to propose, but there weren’t any concrete details in place. She also shared that my sister would be receiving a special engagement ring—the one my dad had given my mom during their marriage. I loved this sentimental touch! My own engagement ring is a family heirloom from my husband’s grandmother, so I’ve always appreciated rings that carry meaningful history.
The Last-Minute Surprise
A few days after my mom shared the news, I got a text from Max on Saturday morning at 10:30am. We regularly send each other funny videos, so I didn’t think anything of it when I opened it. But this time, the message was just an address in Mequon.
I hit him back with, uhhh, tell me more, please.
That’s when he responded: I was planning on 7:30ish, right around sunset. Caitlyn and I will go there probably around 6 to do some fishing. Once I get there, I can show you where you guys can hide so she doesn’t see you. My buddy and I are going in 20 minutes to check it out. Let me know if you can make it, and I’ll send some pics of what it looks like.
I replied, Tonight?!
He immediately responded, Yes.
Luckily, I had no plans!
Since trying to coordinate surprise engagement photos over text can get chaotic, I called Max so we could figure out logistics. The location he sent me was Virmond Park, which is beautiful, but after he and his friend scouted it, I could tell it wasn’t ideal. It was a stunning spot right on Lake Michigan, but there weren’t many places to hide, and more importantly—my sister was six months pregnant. The massive set of stairs she’d have to climb would NOT be her vibe. Also, the wind off the lake was strong that day, which meant unpredictable hair, flying clothing, and not an ideal setup for photos.
A Quick Change of Plans
Max was set on proposing that day, so we brainstormed a backup plan. Since it was a warm April day, we needed a location that was easy to get to but still provided a beautiful, natural setting. He suggested Menomonee Park instead. Instead of fishing, Max could plan an archery date since both he and Caitlyn are avid hunters. That way, it would seem like a totally normal weekend activity.
With the new plan in place, my other sister, Carley, and I rushed to the park to find the perfect hiding spot for surprise engagement photos. The archery range was surrounded by trees, which was great for hiding—except that spring had barely begun, and the trees were still bare. Our “hiding spot” was very obvious.
Good thing I always travel prepared! I keep blankets and towels in my car for things like this, including a camouflage hunting blanket, which ended up saving the day. Carley and I gathered brush, dragged logs, and layered blankets over us to stay hidden. It was a wild amount of effort, but it was also one of those funny moments we’ll always look back on and laugh about.
The Chaos Before the Proposal
As we were getting into position, I set up my phone to capture a video from the top of the archery stand. Everything was good—until the wind knocked the towel I used to hide it in front of the lens. I had to sprint from the woods, climb the stand, fix the camera, and rush back just in time. It ended up being a false alarm—another family had arrived at the park, and I started panicking that they’d unknowingly take the exact table I had directed Max to use for the proposal.
Even worse, they had little kids playing nearby. The last thing I wanted was for them to think two adults were hiding in the woods, spying on them. My sister was also freaking out at this point, so I left our hiding spot to talk to the parents. I explained that we were there to capture surprise engagement photos, and they were super understanding. They even moved to a different part of the park to give us space. Crisis averted!
The Big Moment
Now we just had to wait for Max and Caitlyn to arrive. The final challenge? Making sure their dog, Diesel, didn’t hear or smell us in the woods. When we saw them walking toward the table, we went completely silent.
I had helped Max plan the proposal so that Caitlyn’s face would be perfectly positioned for photos. He was supposed to take a couple of shots first, retrieve his arrows, and then let Caitlyn take a turn. When she walked forward to get her arrows, Max would pull out the ring and get down on one knee. Then, as Caitlyn turned back toward him, she’d see him with Diesel by his side, making for the perfect moment.
Of course, nothing ever goes 100% according to plan with surprise engagement photos—and that’s part of the fun. Diesel’s leash got tangled, and Max ended up a little off from the planned position. Plus, nerves kicked in, which made things even more spontaneous. But once the moment started, Caitlyn was completely in her own world, and I was able to move in closer without her noticing. The raw emotion in those first few seconds was priceless.
An Unforgettable Yes
After Caitlyn said yes (obviously!), I took some additional portraits to round out their surprise engagement photos. I always love to do a mini session after the proposal to capture a mix of emotional and lifestyle images.
What made this even more special was that my mom had literally driven across the country to be there for this moment. As a semi-driver, she’s constantly on the road, but she made it happen. I was able to capture the moment she arrived, which I know my sister will cherish forever.
Capturing surprise engagement photos is always an exciting challenge, and I love helping couples plan their perfect moment. If you’re thinking about popping the question and want to document the big surprise, let’s make it happen together!
📸 Check out the highlights from Caitlyn and Max’s surprise engagement photos below—click on the images to see some hidden surprises! Ready to create chaos together? Book me, and let’s make your dream proposal happen!
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