Alison and Daniel

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How We Met

Alison and I first met on a dance floor in Williamsburg, Brooklyn in April 2012. Alison was out celebrating the birthday of her closest friend, Kevin, when I received a text from a mutual friend Matthew to come join their party at Cameo Gallery.

I vividly remember seeing Alison for the very first time. Short-hair, beautiful eyes, clearly having a great time — I was immediately attracted. But when we were first introduced I thought the guy standing next to her was her boyfriend. It wasn’t until Alison approached me a few hours later that I found out he wasn’t (though not for lack of trying).

I’ll never forget our first real exchange:
[Alison dances up, non-chalant] “What was your name again?”
[Me, surprised and now smiling] “Dan”
[Alison, taking a bold turn] “I think you’re cute.”

That’s all it took. Fast-forward a few days and we’re on our first real date at a restaurant in Brooklyn Heights. Fast-forward three years and we’re getting engaged in Iceland.

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How He Asked

The trick with getting engaged in Iceland is that there is no shortage of beautiful places to ask. There are waterfalls, glaciers, black-sand beaches, green mountain-ranges, hour-long sunsets — it’s hard to go wrong. When Alison and I had set out on a 10-day trip around the country, it wasn’t until the morning of the third day that I finally worked up the nerve to propose and that’s mostly because of analysis-paralysis from me trying to find the “right” place.

There was the time where I almost asked at Seljalandsfoss (where we have some of our engagement photos), but I thought there were too many people around.

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Later that day, we found puffins at dusk at Vik — one of the happiest moments of Alison’s life — but it had also gotten pretty dark and kind of cloudy so it suddenly seemed like a poor choice. And really no one wants their engagement upstaged by puffins.

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About an hour after my second cop-out, I finally had a breakthrough. Alison had brought a Go-Pro on our trip which can take ‘bursts’ of photos — basically like taking a video — which meant I could trick her into documenting our whole engagement. The next morning while we were driving, I asked her if she wanted to pull off the road to take a photo together and she agreed.

After she set up the tripod and camera, she ran into the frame and I nervously got down on one knee. “Oh, are we doing this now?” she asked (she really had no clue it was coming). One short monologue and a “Will you marry me?” later she said yes.

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Our Video

Watch more proposal videos & follow @HowTheyAsked on Instagram for more stories!

Special Thanks

Brasspenny Photography
Photography