proposals

How He Asked

The pictures from our 2013 phones are really not great quality. So this is from our engagement session the following Spring. Photo by Kristin LaVoie Photography

The pictures from our 2013 phones are really not great quality. So this is from our engagement session the following Spring. Photo by Kristin LaVoie Photography

Yesterday was the 5 year anniversary of our engagement! In honor of the occasion, I wanted to share the story of how he asked!


The year was 2013. The town, Chicago. Conor and I had recently moved back to the States after a glorious year living down unda, in Sydney, Australia. While we had lived together when we were there, when we returned home, he got an apartment close to his office, and I moved back in with my parents. So to see each other, we would often have weeknight date nights after work.

That fall I had started volunteer tutoring with an awesome organization, Chicago Lights, located on Michigan Ave. It was a tutoring evening, so when I finished he picked me up and told me we were going to this sushi place in his neighborhood.

We were driving towards dinner, and I notice he missed the turn, and then he turns the opposite direction from sushi. At this point, I’m thinking, “What’s going on? Where are we going? What’s happening?”

We pull up at the Radisson Blu, in the Aqua building (Conor’s favorite building in the city at the time). He says, “Surprise! We are doing a staycation here tonight! There was a flash sale (lol not true) so I thought it would be fun!” This was not that far off from our occasional change up in routine, so it wasn’t completely out of character. But I was definitely deep in my head. “Is it happening? Or is he just being spontaneous? You’re imagining this.”

We get up to our room, and it has a killer view of the Wrigley Building and all of the Christmas lights along river. Even the bathroom had a view! We stepped outside on the balcony and it was freezing, and promptly returned inside. We then looked at the view from the bathroom for a while. Meanwhile, my mind is going crazy in every silent moment staring out the window. We finally got out of the bathroom (thank God!) and found ourselves in a cozy corner looking down at the Christmas lights. Next thing you know he starts saying all of these really nice, loving things, that I couldn’t repeat even if I tried, because a moment later he was down on one knee and I was mess. He asked me to marry him and the rest is history. 💘

I had never been that girl pestering and wondering when it would happen. And it’s interesting, for a really long time I didn’t want it to! We were so happy as things were- I didn’t want marriage to change things. Also, to be fair, I am a child of divorced parents who met in college (just like us!) and I did not want that fate for myself. We had been together for 6 years when I finally felt like we could begin to approach the subject of engagement! I know, I’m crazy. But when the time came, I could not of have been happier or more ready.

What I love about Conor and our relationship is that we know each other sometimes better than we even know ourselves. He told me later, he didn’t even know the night before he proposed, because if he knew, he knew that I would figure it out. So he had to surprise himself in order to surprise me! He had the ring for months before finding the right moment to make it happen. He also knew that I wouldn’t be keen on something large and public, despite the fact that he is super charismatic and thrives in the spotlight. It was a special night that was really just shared by the two of us- which made it all the more meaningful to me.

It’s funny because in someways your engagement is the beginning of your story, even though it can feel like a fairytale ending. There is so much ahead, both beauty and hardship. We have been through so much over the past 5 years (I mean really 11 years now!), and have so much more ahead of us. Being married is the process of falling in love, over and over again. 💖


So that’s our story! I would love to hear yours too! Comment below or send me a note on Insta or FB! Happy engagement season, beauties! -AHS