This Proposal Video Will Make You Cry and Laugh All at The Same Time

funniest proposal ever

How We Met: Jen and I met online in February 2013. I was separated and Jen had been divorced for a few years. I’d just begun thinking about dating again, and she’d nearly given up on finding someone.

I half-heartedly signed up on the dating service but hadn’t completed my profile beyond my name, location, age and a few other details. Jen had closed down her profile but, looking for some information, had logged in to retrieve it. The company’s policies were that when a user did this, their account reactivated for a few weeks.

It was during this brief window that I read her profile.

I was intrigued that she was a wedding and portrait photographer and lived in rural northeast Iowa, a beautiful place of rolling hills, farmland and soaring bluffs above the Mississippi River. She described herself as adventurous and a traveler, and said she hoped to find someone willing to venture to her rural region to meet. Since I’m originally from Iowa, and was living about an hour away in western Wisconsin, it wasn’t that great of a leap to meet her there.

Still, I didn’t contact her through the online dating service. From clues I picked up in her profile, including her username, I did a Google search on northeast Iowa photographers and found her business Facebook page and, on it, her work e-mail address.

I wrote and explained my appreciation for her work and then explained me and my life. Near the end of my message, I explained that we had a mutual friend who lived in her community — another healthcare marketing manager who worked at their local hospital. I urged her to contact this mutual friend and be reassured I wasn’t a creep or a stalker.

Jen contacted me a few days later and said she had chatted with the friend, had liked my message and said we should meet in a nearby community for coffee. We met that weekend and ended up talking for four hours, and one hour past the coffeehouse’s closing time. The staff were kind enough to keep it open just for us, then gently encouraged us to leave by noting, “We closed an hour ago.”

We had a engaging, funny text chat on the way home, and that began a continuing conversation and many dates in the coming months. In spring of that year, she took me for the first time to New York City, and in August we drove to the Pacific Northwest and then down the West Coast to California.

In spring 2014, with my divorce final, I moved to northeast Iowa and Jen and I lived for the summer in her northeast Iowa hometown. Also that summer, we returned to the eastern U.S. where she showed me around Newport, R.I.; she’d lived there a few years earlier and loved being near the ocean (and all that fresh seafood!) Later that year we moved to north-central Iowa to live in an inexpensive rental house and decide what should be our next step, and where our next adventures lay.

How I asked: When I decided to propose, I wanted to use my videography skills to tell a story. The idea for a video began developing six or seven months before we filmed it.

In November 2014, Jen and I attended a performance by a unique Tupperware lady named Dixie Longate. Her show is snarky and hilarious, but also surprisingly poignant and uplifting. And for some reason, that night I tucked away in my mind the idea of having Dixie help with my proposal.

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In spring 2015, I contacted Dixie and asked if she would participate. She didn’t hesitate to say yes and was willing to do anything to help. “I’m a giver,” she said.

I recruited Jen’s nephew, Jack, to be the “hero” and her father, Chuck, to be the “villain.” I reached out to family and friends across the country and asked them to be supporting cast. Many sent short, creative videos of themselves lip-syncing to “Rude” by Magic, which I pieced together to make the first section.

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The second section includes a surprise appearance by Dixie, where — in keeping with her sassy attitude — she tries to convince Jen NOT to marry me. That was by design; rather than having her endorse me, I wanted Dixie to cut me into tiny pieces. I urged her to warn Jen that she would be making a TERRIBLE mistake if she said yes.

The final few seconds of the video are by a young Idaho man named Gus. We’ve never met. On that August 2013 West-Coast trip, Jen and I passed through Wallace, Idaho. It was a memorable stop for many reasons, including a late-night, semi-serious proposal in the parking lot of a Wallace grocery store. Jen said no, but it’s remains a funny memory of that trip.

I was stumped how to include that memory, but in mid-June I posted a request on Spokane’s Craigslist. I offered $10 for someone to go to Wallace and tape a short segment holding a “MARRY THAT GIRL” sign next to a Wallace landmark so it was clear it was Idaho. Gus — calling me “bro” in every friendly e-mail — taped and sent me the final part I needed for my film.

I proposed the evening of July 4, 2015, in beautiful Clear Lake, Iowa. Her family decorated the deck behind our house with a canopy, candles and wildflowers we picked that morning. A group of friends kept Jen away throughout the afternoon so that we could decorate and I could set up the computer.

The diversion to keep her away worked a bit TOO well. Jen was reluctant to leave the lakeside outdoor bar where she and friends had settled in for a nice afternoon of drinks and live music by local musicians (who also knew about that day’s proposal).

Just before we departed, the band — without my urging — played the Ryan Adams’ song “Two”, which is one of our favorites. We danced alone in the sand in front of the musicians, as everyone watched, and then we headed home.

However, Jen thought we were heading for another local outdoor establishment, and wanted to be sure the visiting friends knew its location. They weren’t directly behind us in their car, and as we passed the bar, Jen was concerned.

I told her “We have to stop at home for a second.” As we drove on, she turned to me and said, “You’re acting weird …”

When we got home, I asked her to wait in the kitchen. I went onto the deck, pushed record on the camera that captured her reaction, then invited her out. The video captures her reaction after that point.

After I showed her the video, I already was down on my knees since I had been watching alongside her as she sat under the canopy. I reached behind the computer and retrieved the ring box, opened it and asked her to marry me. Jen said, “Yes. Of course.” Here’s the video to watch that:

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How we designed the ring: Since this is the second marriage for each of us, and because Jen photographs weddings nearly every weekend, she wanted something unique. We looked at traditional engagement rings at area stores, but none interested us. Then, on a whim, we stopped at Grunwald and Kiger, jewelers in Mason City, Iowa, who sell pre-made jewelry but also design custom rings.

We spent more than three months talking about design aspects, including having the gold band reflect Jen’s love for art deco and other designs from the Roaring Twenties. Also, “Frieden” is German for peace, and the band design — when looked at upside down — resembles the familiar peace symbol. Jen also wanted a non-traditional stone, and chose a blue topaz.

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The G&K jewelers did a masterful job of listening and patiently making changes to this one-of-a-kind ring, and the end result is stunning. We’re very pleased we worked with a jeweler who could take our many ideas and bring them all together into a stunning creation.

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