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Planning Proposals: The Element of Surprise

This couple’s proposal story really takes the cake.

Wedding photos by krystal Healy photography|Engagement photos by Love & Light photography by Allison Leigh


Proposals are often the best day of a couple’s lives, second only to their wedding day. And, with the rising popularity of viral videos like this penguin proposal, significant others have had to step it up a notch when it comes to popping the question.

When J.R. Kenna invited his girlfriend Brittany Firman to celebrate their two-and-a-half-year anniversary, Brittany had no idea what he had in store for the day.

They started the day off with a wine tasting at Narcisi Winery in Gibsonia. Brittany didn’t think much of this afternoon adventure because J.R. often schedules fun weekend plans for the couple. “The overall day felt so incredibly normal and so did the days leading up,” she says. “He truly does specialize in romantic surprises without making me feel suspicious.”

At the winery, the tour guide introduced Allison Wilde, a photographer who would be documenting the day to add photos to the winery’s website — or so Brittany thought. J.R. had actually hired Wilde, a photographer that both he and Brittany followed on Instagram, to capture the proposal on camera.

Luckily for J.R., Brittany was completely unaware of his plans. “I saw a photographer and didn't think twice,” she says. “I made a joke about how I was going to ask her to take our photo (with my iPhone) in front of the fountain and didn't notice that she was following us around.”


Eventually, J.R. excused himself to the restroom and returned with a giant Kate Spade bag for Brittany. Then he took out a photo album he’d created of memories the couple had shared over the last few years documenting their first trips, events and memories together.

On the last page, there was a Kate Spade “Mrs.” necklace, and Brittany turned to see J.R. down on one knee. After he proposed (and she said yes) the couple spent the rest of the day with the photographer, who J.R. had hired to document the day. Then J.R. surprised Brittany again with a couple’s massage, dinner at Eleven in the Strip District and a suite at the Renaissance Pittsburgh Hotel Downtown.


Unbeknownst to Brittany, J.R. had been planning the romantic surprise since March when he’d asked Brittany’s father for her hand in marriage. “After a couple a whiskeys and memorable conversation, we had a timeline of when it would all happen,” says J.R.

From there, the future groom was busy finding a ring, a photographer and making the album of “Our Firsts” to show to Brittany before the proposal. J.R. went in to work an hour early every day for weeks, using SnapFish to fill more than 25 pages in the couple’s book of memories from their two and a half years together.

Brittany and J.R. were married at Heinz Memorial Chapel on Aug. 13. And, although it was an amazing day filled with family and friends, the couple will always treasure the intimate moments of the proposal. “I remember so many tears of happiness and shaking with excitement when I finally realized how my life was changing,” Brittany says. “[I was] completely surprised and so totally in love. It was the best day of my life.”


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