The Best Surprise Ever — Our Engagement Story

On an uncharacteristically warm winter day in Chicago, Ryan put on the ultimate proposal. And i’m here to share the entire beautiful story today…

Sarah Koller Engagement 1

We had originally planned to take a trip to Portland together as sort of a “last hurrah” before Ryan started busy season. However, I suggested instead paying a visit home to my favorite city {Chicago} to see family and friends. So with that intention, we booked our tickets and I began to put plans into action for a fun weekend in the Windy City. Little did I know, Ryan had an agenda of his own.

While I was busy making dinner reservations for our friends, Ryan was reaching out to the same crew to tell them he was secretly strategizing a surprise engagement. Our intention was to spend the day with my sister while we waited for everyone to get off of work. So once the day rolled around, Kristin, picked us up as from the airport as planned, but notified us she had snagged a last min hair appointment. For anyone that knows our relationship, this quick change didn’t set off any red flags. So I suggested we go skating downtown at a beautiful rink in front of The Bean instead. Little did I know, this lined up pretty nicely with Ryan’s schedule for the day…

Unbeknownst to me, for the few minutes we were making laps around the rink, Ryan was making eye contact with the hired photographer, scheming to get me to “the spot”— without falling first! To me, Ryan didn’t seem too into the skating thing {after 10 minutes he was ready to go!} so I suggested we walk up to The Bean instead. We made the trek up, and wandered around the city’s landmark for awhile. Before leaving, Ryan recommended we take a photo together and handed his iPhone to a guy that “seemed to know what he was doing.” Jiho {as I would later learn his name} took a photo, then recommended we step up on a picnic table close-by due to the number of people around that day. {It was, after all, a very nice Friday in Chicago!} Although I thought it was a bit odd, I complied, and as I posed with a smile, Ryan made a quick maneuver to his knee and popped out a small box holding the prettiest rose gold ring I had ever seen.

For as much as you think about your wedding day, the engagement itself is something that you never truly plan for. While I vaguely remember a few words mumbled out of my {new!} fiancé’s mouth and hearing clapping from the crowd, those seconds of the proposal were an absolute blur. As the story goes, I somehow managed to give him the wrong hand, and was so in shock, I forgot to say “YES.” {To clarify, I did shortly after-the-fact, but I guess that all just adds to the character of our proposal!}

Shortly following that highly emotional moment, our photographer, Jiho, took a quick engagement photo session around Millennium Park, while Ryan began to unfold our plans for the rest of the evening. Come to find out, I wasn’t the one with all of the plans for the weekend! He had schedule our families to be waiting for us at a hotel a few blocks away, and all of our friends would be joining us for a big celebration at the very same restaurant I had been making plans at. I was shocked! It’s safe to say we spent the next few hours celebrating and sipping champagne with those nearest and dearest to us in pure, engaged bliss!

All in all, we had talked about spending a life together, but the details of making it actually happen were something we never discussed. So the day of the proposal was all the more amazing because of it. Everything that came together for the occasion including family, friends, a professional photographer, and a big party were honestly perfect, and I would’ve have had it any other way. So without further ado, here are a few photos of the day where our futures “officially” started together. Enjoy!

Sarah Koller Engagement 2

Sarah Koller Engagement 3

Sarah Koller Engagement 4

Sarah Koller Engagement 5

Sarah Koller Engagement 6

Sarah Koller Engagement 7

Images via Lily Photography/Jiho Park

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