Our Greatest Adventure Yet

From Neighbors to Everything

How It All Started

Like so many love stories born in 2020, ours began with the unusual circumstances of building bubbles around ourselves during the pandemic. Jackie had just moved in next door, seeking a yard for Mac during those uncertain times. Teddy had built a home there with Lincoln, Oliver, and Jellybean. The two dogs made their presence known by barking through the fence between our yards, with Lincoln popping his head over from time to time.

What started as neighborly favors—shoveling snow and grabbing packages—slowly evolved into something more. After we'd chatted about Spartans and mud runs, Teddy sent Jackie a text a few weeks later asking if she'd join him for a camping trip to Telluride to run the Spartan Beast. This launched our weekly training runs in the Colorado foothills, preparing to tackle the altitude. Training runs were always followed by dinner—after ditching our sweaty running gear, of course.

We hung out for weeks like this, having deep conversations about life, trail running, sharing dinners and drinks. The funny thing? We never once talked about dating or personal relationships.

The Moment Everything Changed

It all came to a head during a moonlight snowshoe trip to Rocky Mountain National Park. In freezing weather, naturally. As Teddy pulled up to Jackie's house to drop her off afterward, he finally asked, "Would you like to get dinner with me sometime?"

Jackie, confused, replied, "We always do that."

"Like... as a date," Teddy clarified.

"Uh, we never talked about that," Jackie said, shutting the truck door and running off into the house.

Smooth, right?

Learning About Each Other

Our Early Adventures

Once we figured out we were actually dating, the real adventures began. Our third date started with us handcuffed together—it's okay, it was an escape room with stupid clowns.

Early in our relationship, Teddy invited Jackie to go skiing in Vail right around Valentine's Day. Jackie enthusiastically said yes. What Teddy didn't know was that Jackie was absolutely NOT a skier, and he learned this lesson quickly on the slopes. For the record, Jackie still can't ski but happily joins ski trips as long as she doesn't get dragged down a black diamond.

Also early in our relationship, Jackie boldly announced that she'd bought a trip to Hawaii and Teddy was welcome to join. Teddy laughed and said of course he was coming—even though the trip was 10 months out and we'd been dating for maybe two months. That leap of faith paid off, because Hawaii became our favorite destination, with three trips together so far.

About six months in, Jackie used HER credit card to insure a houseboat as Teddy promised not to sink it while driving around Lake Powell. The trust was real. The trip was filled with memorable challenges—Jackie's paddle board almost sank, and if you ever want to test a relationship, try anchoring a houseboat against rocks in the middle of a windstorm.

One of our most hilarious early date memories? The time Teddy went out of his way to rent a DVD from RedBox, only for us to realize neither of us actually owned a DVD player. That moment still lives on in our never-ending list of inside jokes.

Our first summer together, we took a trip to Steamboat Springs, Colorado. During a trail run up Fish Creek, we talked forever—about everything and nothing. That's when we discovered we could spend hours together without ever running out of conversation. From that trip forward, all our adventures became these epic brainstorming sessions where we'd make up fictional companies that would save the world, sometimes with theme songs. We became best friends who felt completely comfortable together, laughing constantly and never getting bored.

We became family gossip when Jackie secretly brought Teddy to a Smith family wedding, and we got caught smuggling wine from the reception back to our hotel. But Teddy got the full Smith family indoctrination when he met Jackie's parents for the first time while they bickered in the car during the drive from the train to the hotel.

Building Our Life Together

Adventures and Growth

We've mastered the travel benefits game—gold status, companion passes, airport lounges—and our travel hacking has opened so many doors, leading to adventures we never could have imagined. From local weekend escapes to international destinations, these travels have shaped who we are as a couple. Jackie had been a travel runner for years, and she introduced Teddy to the world of destination racing. Now they've been able to experience this passion together, with Jackie completing her World Marathon Major Challenge and Teddy discovering his love for the sport of marathoning in places like Tokyo.

Creating Our Family

Since that day, life has been a whirlwind of adventure and everyday joys—raising two incredible boys, merging our households, getting Mac accustomed to the chaos, and endlessly renovating the attic. We've traveled near and far, attended way too many kids' bounce-house parties, dressed up in ridiculous costumes for school fundraisers, and spent countless weekends cheering on the soccer sidelines. We paddleboard as a family, attempt to ski together, and always find ourselves at a good concert.

We've watched Lincoln develop his love for art, origami, and especially underwater sea creatures—Jackie now knows more marine biology trivia than she ever thought possible thanks to all of Lincoln's questions, making it one of their favorite activities together. Oliver has discovered his passion for music, whether he's singing, making his own songs, or constantly asking the Amazon speaker to play his latest favorites. This past summer brought a new adventure when we lived in San Francisco with the boys, experiencing "real" city life—yes, we're lovingly poking fun at you, Denver.

What makes us work? We balance each other out, embrace the unconventional, and make even the ordinary moments feel extraordinary. Through all of this, we've learned to be completely honest with each other and built deep trust. We're figuring out this whole parenting thing as a team. What we love most is being best friends and approaching everything as a family unit.

The Proposal

Golden Hour Magic

We'd planned a New Year's snowshoe trip to Sequoia National Park but arrived to find no snow. So naturally, we drove over three hours round trip to REI for new trail runners and gear—because that's what you do when adventure calls.

Teddy had originally planned to propose at the General Sherman tree, until he saw the overwhelming crowds. So we kept running until the golden hour light filtered through the towering trees and Teddy found the perfect secluded spot. He asked Jackie to stand beside a massive tree while he fumbled and fumbled and fumbled with his camera setup—an unusual amount of effort for a simple picture.

"What are you about to do?" she asked suspiciously.

And then, with the camera rolling, Teddy got down on one knee.

For the rest of the trip, every time we stumbled upon a stunning landscape (and eventually found snow), we laughed, saying, "This would have been a great place to propose!"

Why River Bend

Finding Our Spot

After originally considering California, we started searching Colorado and discovered River Bend through a referral from another venue owner. The moment we saw the grounds and heard Chris and Sarah's vision, we knew this was our place. Our love for paddle boarding, especially on Kauai's rivers, made this riverside location speak to us immediately. And those cliffs—we went exploring right after our tour, naturally.

Lyons is famous for being the place "millions of people drive through every year but never stop, while heading to Rocky Mountain National Park." The night Teddy officially asked Jackie on their first date was the same night we first visited RMNP together. We returned there for our engagement photos. For our wedding, we decided you should all finally stop in Lyons instead of just driving through.

This venue perfectly captures who we are—unexpectedly beautiful, hidden in plain sight. It's comforting yet embraces our adventurous spirit. The property has a history of resilience, having flooded years ago before emerging as this beautiful space. Like us, it's about new beginnings rising from life's challenges.

What's Next

We honestly don't know how life could get better than what we're already building together. Watching the boys grow has been pure joy and chaos, and we're excited to continue this adventure as a married couple.

This wedding day represents the beginning of our next chapter as an official family unit, and it's about bringing together all the people we love, many of whom have never been in the same room together. It's about laughter, connection, and celebrating a love that has been built on adventure, resilience, and a whole lot of trail miles.

We're looking forward to watching the bond between Mac and Lincoln continue to grow, cheering from the sidelines at more school activities and soccer games, and waiting for the day the kids can carry their own camping gear—because camping as a family is something we absolutely love doing together.

As for the future? We dream of a hot tub, where we can drink coffee in the mornings and wine in the evenings. We look forward to watching the kids grow, facing life's challenges together, and being that grumpy but lovable old couple that constantly writes letters to the city—not to complain, but because we just want things to be better.

Our future dreams also include always working on that retirement plan, Teddy getting old enough to qualify for the Boston Marathon—he's going to hate that joke, and there will always be more travels ahead, because that's just who we are.

Here's to more trails, more laughter, and a lifetime of adventure.

Most importantly, we're excited to keep being best friends, laughing together, and tackling whatever adventures—mundane or magnificent—come our way.