Jennifer and Kyle

Image 1 of Jennifer Claire and Kyle David

how they asked

It’s the classic tale of Analyst meets Artist…
Kyle = Books, Business, Button Downs (Biceps?)
Jennifer = Dance, Dedication, Documenter (Dreamer!)

We were colleagues at an Ad/Tech start-up, in Chicago. Both of us had just relocated to the windy city for our jobs, and as we were settling into this new chapter, we found ourselves going out with co-workers quite a bit. One evening we went to Trivia Night, with a group of people from work. As the night progressed, Jennifer impressed Kyle with her Disney movie and world geography knowledge! And Kyle made Jennifer feel special, desired, had her laughing constantly… and slowly seduced her with the sweetest puppy dog eyes.

We had actually known each other for a few months and were friendly, but it was that night, on the train ride home, that we somehow reached a deeper level of connection. We both remember when it clicked… Jennifer said: “I enjoyed tonight, but I’d really rather spend my Fridays at home in PJs, with some Netflix!” Not exactly the most romantic words we’ve ever uttered to one another… but it was the truth, and it was then we realized were quite aligned.

And thus began weeks of binge watching old TV shows with my boo, every evening after work – namely: LOST. Until we decided we were being rather lame and thought that we should go out on a real date, like a real couple would… The Zoo Lights at Lincoln Park and then a comedy show at The Second City. There was romance, laughs, and love… Yes, you could already feel the love. I had so much comfort and confidence in what was blossoming… And I could sense he felt the same.

Since making it official, we have traveled around the country together, learned to swing dance, adopted two guinea pigs (companion animal options are limited when your partner has allergies!), gotten to know each other’s family, eaten our way through Chicago and other cities we have visited, become a part of one another’s inner circle, celebrated big wins! and mourned a few losses… We worked together to build a business, purchase our first home, and most recently, we added a third guinea pig to the crew! (Our Three Little Piggies: Aldo, Pasquale, Lucca)

It’s been a whirlwind couple of years for us! And our favorite part of the relationship is that we’re still learning new things about each other all the time. We may not have a ‘meet-cute’ story for how we got together, but our lives are rich with experience and we’re excited about our future together. We’ve had a great ride thus far, and I can only imagine things will get better!

Image 2 of Jennifer Claire and Kyle David

how they asked

It had been a very long year for us both… changing jobs, attending various family functions, working to launch a photography business, and keeping the balance (and sanity!) month after month. So when December rolled around and I realized we hadn’t really done anything for US – no trips, weekend getaways, or even a staycation – I was pretty disheartened and upset. And, as embarrassing as it is to admit, I may have had a little breakdown over this… I threw a fit and declared that we needed to prioritize a trip. And we needed to do it SOON!

It’s not my most becoming characteristic – tantrums! – but it was certainly effective in this case! And Kyle took it very seriously, booking a trip to Park City, Utah the VERY next day. He gave me a card a few days later on our Two Year Anniversary, and in it there was a number: 84060 (this was a little puzzle for me to figure out… a zip code!) It wasn’t a hard one to crack and I gathered where we would be heading the following weekend; I was excited to be celebrating two years on this trip! And since it was such a last minute thing, I didn’t think much more of it (I certainly wasn’t expecting a proposal!) I was just delighted to be heading West and to be immersed in the mountains…

Kyle was going to have a busy week of work before we departed, so he asked that I plan a little agenda for us, in preparation for the mini-vacation. There are so many amazing recreational activities to partake in, but when I discovered dog sledding, I was immediately sold on it! I let out a tiny squeal of excitement, then sent the information to him, and we booked our first ever husky ride adventure at Thousand Peaks Ranch, with Luna Lobos Dog Sledding! But little did I know, Kyle also did some planning and decided he wanted to offer a marriage proposal to me mid-ride! AND he wanted the moment documented by a photographer, as well…

Image 3 of Jennifer Claire and Kyle David

By the time we were out on the trail and taking in the most amazing, expansive, utterly breathtaking scenery… I was glowing and giddy and glued to the moment. I had no notions of what was to come… I was in heaven and doubted that life could get any better! Really and truly, I was just so pleased in that moment. And! I had anticipated that I was going to absolutely love this experience, so I actually purchased a GoPro to capture some of the journey.

Image 4 of Jennifer Claire and Kyle David

When we reached the halfway point, we stopped for hot cocoa and there were a couple other ‘tourists’ that were there taking a break on the recreational trail, as well. I played with the pups and took some photos with them… and shortly after we had stopped, I was pulled away to have a private moment with my boo.

Image 5 of Jennifer Claire and Kyle David

Image 6 of Jennifer Claire and Kyle David

Image 7 of Jennifer Claire and Kyle David

At the time I was confused why he would be leading me away from the dogs (he knows how much I love animals!) and I was excited that the other folks were taking photos of me with them! But when Kyle told me, “Don’t worry, they are going to keep taking pictures!” It hit me like a ton of bricks… !!!

Image 8 of Jennifer Claire and Kyle David

Image 9 of Jennifer Claire and Kyle David

Image 10 of Jennifer Claire and Kyle David

He quickly got down on one knee… and asked to spend our lives together; to marry him. (Finally!) In all honesty, I don’t remember a single word that either of us said. I was just so completely surprised! But I’m pretty sure he proposed marriage, because he presented a ring and we kissed, snuggled, loved on each other. And I said yes! (Yes! YES YES YES YES!!) So, yeah… I’m pretty sure that’s what went down. The ride back to the start of the trail was such a fun one…

Image 11 of Jennifer Claire and Kyle David

Image 12 of Jennifer Claire and Kyle David

Image 13 of Jennifer Claire and Kyle David

Image 14 of Jennifer Claire and Kyle David

You can see such a shift in excitement and emotion from the first part of our video to the last. So happy we have that, as well as the AMAZING photos from Carla Boecklin. …We love reliving these moments!

Our Video

Special Thanks