Wedding Wednesday: Our Engagement Story

Dave and Jessica at a lake house in Vermont sharing the news of their engagement

Now that I’ve told all of my friends, family, and communities (IG subscriber family, email subscribers), I wanted to make it official and share how Dave proposed here on the blog. 🥰 While I don’t know if I’ll have a wedding-related topic to discuss every Wednesday, I do plan to share some thoughts and inspiration throughout our engagement here on the blog. In this first installment of Wedding Wednesday, here’s the story of our engagement…

Dave proposed on Christmas Eve right before we left for our Canadian road trip on Christmas morning. Between packing and getting ready for two weeks away, telling our friends and family, and then wanting to savor our trip and be in the moment, somehow two weeks went by before I spilled the beans on Instagram.


Yes and no!

We went ring shopping back in August, so I knew it was coming. (Again, shared a little glimpse of that in real time for Instagram subscribers!) Since I picked out the design of the ring, I told him to try to surprise me with the proposal part. I was certain it was going to happen while we were in Canada, but he proposed at home on Christmas Eve, just the two of us- and Marley. ❤️

Nothing elaborate, no hidden photographer for candid photos. And honestly, it was just right for us. I was going to say “Nothing fancy,” but we popped a bottle of Dom afterward that Dave had hidden outside! 🍾

In hindsight, it took so much stress off the trip, for both of us! His original plan was to propose somewhere in Canada, but he felt uneasy about not having a specific plan. For him, trying to find the ‘perfect’ place and time would have been a lot of added daily stress. Especially when traveling, a lot can go wrong and emotions can run high so he decided to do it before we left. And for me, wondering if it was going to happen at any given moment would have been a lot of anxiety, too.

We celebrated Christmas with Dave’s family on Friday the 21st and we had plans to visit my family for a belated holiday celebration in January once we got back, so it ended up just being the two of us at home on Christmas Eve. I believe he originally wanted to propose in Quebec City, but since that was the last leg of our trip and we would have already been in Canada for a week at that point, he decided to do it at home that night.

For the night we do gifts together, we always make Beef Bourguignon and watch a Christmas movie. Since Christmas Eve was on a Sunday, we spent the day watching football and getting packed for our trip. While I was planning all of my outfits (that I thought could all possibly be what I was wearing when he popped the question in Canada 😂), Dave was busy cooking in the kitchen all day. And simultaneously getting ready to propose, haha.

I had a couple of rogue thoughts pop into my head throughout the day, like, “Is he going to propose today??” I could just tell he was acting really giddy, but I figured it was the Bears’ win and the excitement for our trip.

When he told me to ‘not worry about the dishes’ after we finished dinner, I knew something was up, but again, chalked it up to wanting to open gifts. I kept wondering if the ring was actually under the tree this whole time, but nothing looked like a ring box.

Between the rush of seeing Dave open all of his gifts from me and him knocking it out of the park with my physical Christmas gifts, I had actually forgotten all about my suspicions. We were missing a few toys we thought we ordered for Marley so I didn’t think anything of it when Dave said he forgot something for her.

She followed him into the guest room and I heard him say “Go show Mom!” She walked out with a monogrammed Foggy Dog bandana that said “Mom, will you marry Dad?” 🥹

Jessica Sturdy sharing the details of how Dave proposed at home.

And then Dave came out with the ring behind her. I don’t really remember him getting down on one knee, but he swears he did. I was sitting on the couch and Marley was wedged between us and the coffee table, so I guess it just seemed like he was at my level. 😂

Then, he snapped a quick photo to send to his family, as they all knew it was happening that night. Why was I wearing a cowboy hat, you ask? 😂  Well, that was the last gift I had opened before he went to ‘grab one thing he forgot for Marley.’ In hindsight, I should have washed my hair and spent a little more time on my makeup that day. 🤪

Speaking of photos, the one thing I’m kind of bummed about is that we only took two selfies together on our entire trip through Canada. One was quick before walking into a dinner recommendation from friends to show them we went. The other was in front of a cute alley in Quebec City but had absolutely nothing to do with getting engaged. Couldn’t we have thought to have someone take our photo one single time??? 😅 Ugh.

I feel like since I have to take photos of myself for work constantly, I’m never trying to take more. Not to mention, I get so embarrassed taking photos in public. Everywhere we went was pretty slammed and I always hate interrupting other people’s experiences, so I never thought to have anyone take our photo. I also didn’t want to be that girl that was leading with the ring and trying to flash it in every photo, you know?? No shade at all to those that do, but it just doesn’t feel very *me.*

In hindsight, I feel like that’s part of the reason that I waited so long to ‘announce’ the news. I kept thinking we would get a cute photo at some point during the trip and I would use that to share a little life update.

On our last night in Vermont, I told Dave that we had to get a picture together and I would take it with my iPhone and tripod. (And I thought I’d wear my new hat as a little nod to the funny Christmas Eve photo… 😂🤠) Go figure, my remote battery was dead and we were QUICKLY loosing light before the sun set. Not to mention, it was absolutely freezing and so windy that my tripod was blowing over. It was pretty laughable! Maybe this just means we need to have actual engagement photos taken here in Chicago?!

Anywho, we are planning a shorter engagement and doing things a little bit differently than most! If you have any specific wedding-related questions or something you want to see, be sure to let me know in the comments below. It will help me better understand what you want to see so I can plan my content accordingly! xoxo

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  1. 1.26.24
    Jessica Hermanson said:

    Happy for you!!