Madison Wisconsin Proposal

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When we aren't crafting new recipes in our cozy kitchen, and visiting the most jaw-dropping WI wedding venues, we're tap-dacing across the keyboard to bring this tip filled blog to you!

oh hi! We're Olivia & Bryan

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A Madison Wisconsin proposal so thought out, so elaborate, and so tear jerking. Family flew in, custom crossword scavenger hunt puzzles were made, and there was even a surprise party

A diamond ring sits on top of crossword puzzles

On a sunny March afternoon- one where the snow had finally melted and one’s soul was brimming with the feeling of spring, it all happened. It started with Rachel getting into a car where I (Olivia) sat. Rachel had never seen me before but in her classic warm-hearted fashion, accepted that I was a new friend. Little did she know that I, Bryan (the other half of O & B Photo Co), Jake (her soon-to-be-fiance), and their family’s had had a group text going with a detailed plan.

A man sits on a chair in the lobby of Graze Madison

Two years prior, their first date was at Graze, a restaurant in downtown Madison (with the best bibimbap in the world according to these two!). Rachel has a very distinct memory of walking into Graze and seeing Jake for the first time. He was waiting for her in a chair right inside the entrance. Take note of this detail- it’s important.

Now, Jake was again sitting in a chair at the entrance of Graze, waiting in nervous anticipation. Meanwhile Rachel was working through the crossword puzzle scavenger hunt that led her to meaningful places around Madison.

Here’s how it went.

Rachel went to get her nails done with her friend, Emily. She thought this was to help Emily get ready for her upcoming trip to Florida – Spoiler: it wasn’t. When she got home, Jake wasn’t home. In his place there was a typed note in a bouquet of flowers. She was instructed to dress cute and was increasingly annoyed when Jake didn’t answer her phone calls or texts. 😉

Unique Proposal Ideas

Next, Emily walked Rachel outside, where she spied a strange looking man standing outside a car. As she walked closer, she realized it was Jake’s best friend, Taylor, and a woman she didn’t know taking pictures (hi, Olivia!!!)

Emily handed Rachel a crossword puzzle for her to solve; Rachel and her family love doing crosswords together. Rachel, Taylor, and Olivia piled into the car and started out on a “scavenger hunt” to various places of significance in Rachel and Jake’s life.

Scavenger Hunt Marriage Proposal in Madison

Stop Number 1: The Madison VA, where Rachel did her residency and works currently. Here, some of her best friends were waiting to surprise her. Excited squeals filled the air. They gave her the next crossword puzzle, which provided the clues to stop number two.

Stop Number 2: Jake’s old apartment, where his family was waiting for Rachel to arrive. They showered her with hugs and handed her the next crossword puzzle.

Stop Number 3: This crossword led to Rachel’s old apartment. There she found her family waiting with signs and lots of hugs! They gave her one last puzzle – the one that would lead her to the most important location in Madison.

A view through the front windshield of a car

Stop Number 4: The final crossword took them to Graze. Warm sunlight streamed down on Jake as he sat in a wooden chair. Bryan snapped this epic photo (one of our most favorite photos EVER) as Rachel stepped out of the car. Family and friends had transformed the lobby of Graze into an absolute fairy tale of cascading eucalyptus, white roses, and deep red ranunculus. Keep scrolling for the most unique Madison, Wisconsin proposal!

As Rachel swung that door open, Jake could not longer handle the anticipation, and leapt off his chair. He rushed to Rachel and grabbed her into his arms. If there hearts weren’t beating audibly, ours sure were;). He gently led her to the eucalyptus arch and twinkle lights. In the same place where they had first met, Jake got down on one knee.

She said yes:)

A man kneels during a marriage proposal at Graze Madison

Loving the city vibes? Wait until you see this rooftop wedding!

After photos at the Capitol Square, they headed to an AirBnB where all of their families and friends were waiting to celebrate them. Rachel says – It was a day we will never forget filled with the people we love the most in the world.

A large group poses for a photo during an engagement party

Jake and Rachel- thank you for trust the two of us with your Madison Wisconsin proposal. Jake and family, for bringing us in on your top secret mission and having us plan with you; Rachel- for not even questioning the strange woman sitting in the back seat of your car. It all led to to the most beautiful moments.