Stephanie and Jamie's Amazing Double Proposal

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How We Met

Stephanie has always been the girl who had a specific “type.” It wasn’t until two years ago that some coworkers banded together to encourage her to date outside of her “type” that I stepped in. I messaged her first on a dating app and waited more than 5 days for a response! At first, my hopes and dreams were dashed. Once she did respond, I was impressed by her directness and charming banter. She immediately wanted to go to dinner, and wasting no time we did.

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This is where someone usually says “the rest is history.” This wasn’t the case for us. I thought Stephanie was wearing a really silly hat and she thought I was the epitome of unfashionable. We chatted and got along pretty well, but neither of us were really certain the spark was there. After a second date at a cute restaurant in Washington Heights, and a third, rock climbing at Brooklyn Boulders, we started to see the spark shining through. We both had the opportunity to show our competitive streaks, but also to be vulnerable with one another. Once I met Stephanie’s dog and cat though, I was really sold.

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How They Asked

Stephanie and I both grew up dreaming about being proposed to and having beautiful engagement rings. That meant we knew there would be two proposals! I asked Stephanie to marry me in a quiet proposal at home, which tied into her interests in poetry and travel. She really surprised me one week later.

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I was at work the last day before we were going on vacation together to visit my sister. I remember counting down the minutes until the end of the work day when Stephanie’s best friend called me and asked me to come downstairs. She handed me a beautiful Erin Fetherston dress from Rent the Runway, along with my make-up bag and two different pairs of shoes (Stephanie is nothing if not prepared!). Once I was ready, a car pulled up and whisked me off to an apartment building on the west side of Manhattan, and Stephanie told me to buzz the fourth floor. Heart beating with anticipation, I climbed the four flights and opened the door to a magical all-white loft space. Stephanie was waiting at the end of an aisle of flowers in a gorgeous white dress and I just remember thinking “This is what it’s going to feel like to get married!”

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Stephanie proposed to me in front of a table strewn with flowers and candles, with the ring sitting in a beautiful glass box from Anthropologie. I barely glanced at the ring before exclaiming “Yes!”. We popped champagne and relaxed for an hour before all of our closest friends arrived to celebrate and toast our (double!) engagement.

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Special Thanks