Our Proposal Story

His and Hers stories from the best day ever

Do we have a story for you…

Come on in, pull up a chair and get comfortable. This might take a while. We’re so excited to share the story from our proposal. The best day ever! Feel free to scroll to the bottom to watch the video of the whole day.

Her side…

Wow…where to even begin?

Let me first start by saying, I always assumed Jake would propose on our anniversary which is Halloween. I was getting VERY impatient with the process. I’m not one to be patient and I don’t like surprises when I know they’re coming.

So…October 3rd rolls around. We had been planning a girls day with two of my best friends Anna and Dani for almost a month. Anna is a full time photographer (and our wedding photographer!) and had offered to do a content swap but make a whole day of it.

The plan was to wake up, get brunch, go thrifting, and shoot blog content together (the easiest way to get me looking cute in public.) After we shot fall sunset photos, we would go back and watch romcoms and eat takeout. Sign me up for the best day ever.

Let me just say, we really did have the BEST day. First, Jake made me my breakfast in the morning. Still, nothing seemed out of the ordinary. I left and headed brunch. At the end of our meal, our waitress came up to our table and said “I was just informed that someone called in and took care of your entire tab.” We all completely freaked out. It ended up being Jake all along. 

While thrifting at St. Vincent DePaul I even picked out a T-Rex toy for our wedding cake topper AND a hexagon ring box to keep on my dresser. Still, I had no idea what awaited me…I was just REALLY ready for it to happen.

After a full day of fun, we went back to Anna’s house to freshen up. It was sprinkling and gloomy all day so I needed to redo my hair and makeup to do fall blog photos. Still, I had no idea what awaited me. I just thought we were rushing to the park to make it before sunset.

We pulled up to Olin Park in Madison and shot some cute photos before Anna suggested we walk further up the trail to the “perfect spot” she knew of. I always trust the professional! Deeper into the trail I see a sign and a pink rose. I thought “What the heck is that? Why is there a rose in the middle of the forrest?” The sign read “My dearest Allie.” And it hit me like a brick. It’s how Jake starts all of his letters to me. I felt like the wind got knocked out of me and I started sobbing. My knees were shaking and I remember thinking to myself “Ok. This is happening. Slow down and take everything in.” The signs lead through the forrest. Adorned with roses and candles.

Each sign read a line from Jack & Sally’s Song in Nightmare Before Christmas.

My dearest [Allie],
If you don’t mind…
I’d like to join you by your side.
Where we could gaze into the stars
And sit together…
now and forever,
For it is plain as anyone could see…
We’re simply meant to be

We then came to a parking lot where Jake’s dad and older brother, Bryan, had his van set up with a projector inside. He told me to sit down and that there was a surprise for me. He turns on this video of adorable clips from different movies. I quickly realized that Jake had produced the entire movie with clips from films we’d watched together and mean a lot to us. It was the most thoughtful thing I’d ever seen. At the end, the movie said to sit in the back of the trunk because we were going for a ride. 

That’s when “Can’t Take My Eyes off of you” starts playing (I found out later he’d recorded a version of HIM singing it!) As we drive down the road, his brother Bryan played the trumpet, and our family and friends started a flash mob singing to the song. People came from far and wide to (safely) celebrate with us. I was a total wreck and sobbed.

Then the van stopped and my dad grabbed my hand and says “Ok! We gotta go! We gotta run!” So I run with my dad to a clearing and I see Jake in a white suit and a crown on a FREAKING HORSE. I thought to myself “He totally WOULD go all out with a horse!” He gets off the horse, surrounded by our closest friends and family and gets down on one knee. With the biggest smile on his face, he pops the question with the gorgeous ring we designed together. He was cool as a cucumber (which I wasn’t expecting at all!) and I was a weepy blubbery mess.

Then I said “YES!” Because there has never been a doubt in my mind that I’d marry him. 

Next thing I know I’m on the horse (her name is Lightning) getting whisked away by my prince. At some point someone put a crown on my head. Lightning even wore her pretty girl unicorn horn for the occasion.

Our friends and family met us in the parking lot for a picnic that Jake had arranged with sandwiches from our favorite place. He even handed out thank you cards to each individual person. He is truly the most thoughtful person I’ve ever met.

When I arrived home, there was yet another surprise. Friends that couldn’t make it had submitted videos congratulating us on our engagement. Even our therapist and our jeweler! It was the sweetest surprise and truly the best day of my life.

His Side…

Once Upon A Time, there was a ridiculous young man with the hopes of engraving an experience of a lifetime in the memories of his Queen. The idea was simple enough: Do something completely outrageous, blow her mind, hopefully she says yes, and get her to ugly cry tears of joy the whole time. Executing that was a bit more involved.

Throughout our entire relationship, inspiration would strike and ideas would get written down in one of my notebooks. Anything from song lyrics and movie quotes to sandwich orders and location scouting missions all to create ONE BIG MOMENT. Armed with ideas, I began planning out the details and figuring out how in the hell I could maaaaaaybe pull this thing off.

The Plan

The Game Plan was to have Allie arrive at the park and walk through an enchanting trail with custom signs that lead her to a screen. On the screen would be a video featuring movie clips that mean a lot to us and tell our story and, afterwards, tells her to sit in the back of the van for ‘one last surprise’. The van then crawls along a short service road while “Can’t Take My Eyes Off Of You” by Frankie Valie plays on a portable speaker. As the van crawls, friends and family jump out and perform a few lines from the song until the van reaches the top of the hill. Everyone runs with Allie to the clearing on the top of the hill where I would be on a horse performing the rest of the song and ultimately popping the question soon afterwards. Simple, right?

Leading Up

First mission: There really wouldn’t be any proposal without a ring. SO, after Allie gave the green light on our ring design, I had to wait for the production to be completed. After I picked up the ring, I went to Olin Park to run through my plans and get some practice ‘bending the knee’ to my future Queen.

Second Mission: secure the photographer. This wasn’t just any ol’ photographer. No one could have better fit the job than her best friend, Anna. She had weddings to shoot most weekends so I knew it would be important to get on her calendar ASAP. First, I booked her for August 29th but then the ring wasn’t done yet. Then I booked her for September 17th but I didn’t have the horse yet. Finally, I asked her if October 3rd was available and after she said it was open I said BOOK IT! We would then continue to scheme together, lie together (with good intentions), and dodge any inclination from Allie that we were working together.

Third: The perfect location. One day I wandered into Olin Park, climbed the hill overlooking the lake and the capital, and something just felt magical about it. I found the perfect stage for my plan. I worked with the Parks director and the City of Madison to reserve the park but we ran into some obstacles. The biggest question….”So, do you….um….allow horses in the park?” and was met with a “No.” every time. I begged, I pleaded, I readjusted my timing until after the park’s events and finally got the all clear to have a horse on the property with some conditions: The horse could only be out of the trailer no sooner than 6:15pm and for 15 min total.

Fourth: The horse. I posted on a Facebook Group that I was in search of a horse for a proposal and got a hit! Over the next few weeks, I went to visit the owner and her horse, Lightning, to get to know her, practice some riding, and have an absolute blast. We would brush the horses, clean up poop, feed them, saddle-up, and hit the trails. I even practiced the whole performance & proposal sequence with the owner posing as Allie! They respectfully declined so that Allie could have a chance to answer first.

Fifth: One last major piece was to gather our friends and family to share in the whole event. As one of Allie’s main requests, I couldn’t resist and sent word to the farthest reaches of the kingdom. I had prepared a Google Doc that had my whole plan with timestamps, satellite maps, schematics, play-by-play, lyric assignments, and more. Once that was ready, I sent it out to our VIPs and scheduled virtual meetings.

Sixth: Preparations (signs, props, projectors, etc.) I worked with my family to get it all done. We cut and painted the signs while my sister made the vinyl letters. I worked with the neighbor to use their small but mighty projector and tested out all the equipment.

The Big Day

When Allie woke up, I wanted to have a nice little breakfast prepared for her. She came into the kitchen to her favorite blueberry & cinnamon pancakes with breakfast potatoes and a ‘mock-mosa’. It was delicious and not terribly out of place so she enjoyed her breakfast as normal and got ready for her girls day.

As soon as she left I ran upstairs to begin printing my Google Docs, Horse waivers, permission slips, play-by-plays, sandwich order receipts, and anything else I could think of. I finished with a few minutes to spare and made some ramen while Luna and I watched an episode of the Office. It was a peaceful moment in a chaotic morning.

Finally, it was time to gather the troops at the park. We had teams of people setting up the projector, hammering & putting together the signs, adding flowers, and finding spots for rehearsal. We were getting ready to do a second run through – this time with the van – and it doesn’t start. The battery was dead after running the projector and equipment for so long without the engine. WELP.

After jumping the van, I realized that I had made the biggest mistake of all – I FORGOT THE RING. Yelling up the hill to my uncle who relayed the message to my friend, I had no time to waste. So, after I was pants-down in my car changing into my white suit, my friend shows up with the ring, chuckles a bit, and runs back to his spot. NOW, everything was in place.

I was so excited for the big moment. I knew the lines and Lightning was ready. I felt cool, calm, & collected. Finally, it was showtime. I sang my heart out to the young woman I had come to love so much and was thrilled to see our loved ones gathering around us. I had never felt so much exhilaration in my life. After the song faded away, I dismounted the horse and walked over towards Allie. I didn’t feel any anxiety, any nervousness, or shaky knees as I expected to feel. Instead, the only feeling coursing through my body was crystal clear focus and peace. Suddenly, I saw flashes of our entire relationship that lead up to this moment. I knew this was it, she was the one. Afterall, I had a pretty good feeling she’d say yes!

The whole kingdom rejoiced when Allie ugly cried her way through a confident “YES” and time seemed to stop again. All of this planning, all of the effort, the challenges, obstacles, setbacks, and details had finally played out and the moment was finally a part of history. There was so much joy and laughter in the air that I remember thinking to myself how ‘right’ this feels. This group of people, on this day, celebrating this moment just felt like pushing the final piece of the puzzle in. It was getting a bit dark and people needed to wrap up and make their drives home when Allie got one final surprise.

The entire experience was everything I imagined it to be but seemed to fly by. After all, I was only really a part of it for the last 120 seconds or so. It felt like a flash to me which made me all kinds of ways. I lived in the moment, I got the girl, and everything played out perfectly. Really, that’s all I could ever want. What a spectacular day!

Watch our proposal!

Photos by Anna Marie Photography