Caitlyn O'Connor Caitlyn O'Connor

Our Love Story

Jim and I first met over 14 years ago during Spring Break in Bethany Beach, Delaware. We were introduced through my best friend and college roomie, Meg. Throughout college, we’d randomly meetup at football games, concerts, and festivals and always had a blast.

Fast forward to 2016: we hadn’t seen each other in over five years. The start of that year had been a whirlwind for me—ending a serious relationship, having a huge job opportunity in CA fall through, and, most painfully, the unexpected loss of my sister, all within 3 months. It forced me onto a deep healing journey, and by the end of the year, I had finally found my footing: a great new job, a cozy apartment with one of my best friends, and a stronger sense of intuition and confidence. I was feeling really comfortable on my own and had set new, non-negotiable standards for myself when it came to dating (which ultimately led to me being a very happily single wing woman for my girlfriends).

One morning at the end of November, Jim was on his treacherous commute to work from VA to MD, when a frantic woman in Bethesda (it’s me, hi 🙋‍♀️) darted across the street right in front of his car to go get into hers. He was annoyed at first—until a few minutes later, he pulled up next to her at the stoplight and realized it was me!😆

He started waving and shouting from his car as I, completely unaware, kept checking my phone and ignoring his calls. Later, I saw another missed call from him and texted, “Hey stranger, I think you’re pocket dialing me!” assuming no sane friend would intentionally call me at 7 a.m, let alone one I hadn’t spoken to in years. Turns out, the school I was teaching at was directly across the street from Jim’s office building. That afternoon, he stopped by my apartment for happy hour, and we caught up as if no time had passed.

A couple of weeks later, he came out for my roommate’s birthday party, where one of my fav cheesy 90s cover bands was playing. While everyone else was drinking and sitting around talking, I heard a song I loved come on and begged everyone to get up and start dancing. Jim was the first (and only) person to hop right up, grab my hand, and spin me around the dance floor—and the rest is history.

Just kidding! As we’d later learn— real love stories aren’t all rainbows and sunshine. Ours required a lot of inner work, expansion and rebirth, and learning to embrace the full spectrum of emotions. Despite our instant connection, we quickly brought up each other’s triggers and shadow sides in that first year of dating. By the end of the school year, we had broken up, and after years of talking about it, I finally decided to move to Colorado that summer. 

Ironically, the moment we broke up, we started running into each other ALL over Bethesda (for the first time since before we dated). I even tried taking different routes, and there he’d be. It felt like the universe wasn’t quite done with us yet.

After my move, we kept in touch, talking almost daily and becoming best friends. A few months later, I got a job offer to travel around the world as a private educator and child development coach, working with a family of inspiring entrepreneurs…one of whom happened to be a famous world-class Love Coach. This job took me out of my comfort zone to experience all kinds of new places— from Burning Man, to ancient ruins in Europe, to Kimbal Musk’s wedding in Spain, to the beaches of Mexico, to the streets of Paris, to philosophy, psychology & genius network conferences, to tiny villages in Whales…it opened me up to a caliber of life, relationships, community, and aliveness I’m not sure I previously believed existed. This family hadn’t been handed this life either—they had created it from the ground up. In my time working with them, I experienced a range of new cultures and learned about people from all walks of life. I made connections, met mentors, and gained friends that remain some of the most impactful people in my life today. At the time, I didn’t realize how much I was growing and changing…or how my relationship was evolving in the process.

Meanwhile, Jim was also frequently traveling for work at the time, and it was rare for us to be in the same place at the same time. We started coordinating our schedules and spending weekends together whenever we could. Then, against all odds, that’s when we got back together. Unlike the stories where long-distance brings out the worst in people, this had the opposite effect…it forced us to grow up, communicate better, and connect on a deeper level. It also didn’t hurt that we had access to one of the world’s leading relationship coaches (shoutout Annie Lalla), who challenged our beliefs about love and empowered us to grow and evolve together and individually in ways neither of us could have imagined on our own. Deeply inspired by the impact, I later pursued my master’s degree & coaching certifications to become a relationship coach myself.

In 2019, Jim and I moved to Colorado (together this time) and shared our first homes in the Front Range. After surviving the pandemic, we decided to take off on a two-year remote work-travel adventure, living everywhere from Alaska to London. When we returned, Jim proposed outside in the rain on New Year’s Eve 2022 (if you know me, there are few things I love more than frolicking around in the rain).

Shortly after, we moved up to our dream little mountain town in Colorado, where we now live amidst the forest, mountains, and an amazing conscious community.

This past September, almost eight years to the day after Jim saw me in traffic, we tied the knot surrounded by our loved ones in a canopy of trees in Virginia.

Our shared love of nature, travel, art, and live music sparked our connection, but our commitment to growth, curiosity, play, and consciousness is what’s kept us together.

If you’ve made it this far, here’s what I’ve learned: Love isn’t meant to be easy—it’s meant to be worth it. Never settle for anything less than a love that inspires you, challenges you, and feels like home wherever you are.

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