From Friendship to Finish Lines with Tyrand and Jen: A Fleet Feet Training x CES Love Story

Some love stories begin with a grand romantic gesture, while others start over casual lunches and shared miles. For Jen and Tyrand, their journey together began at a bar crawl, evolved through lunch meetups, and flourished into a shared passion for running — one that has taken them across finish lines, around the world, and ultimately, to a momentous proposal at the 2024 Disney Dopey Challenge — the notorious challenge where you tackle a 5K, 10K, Half Marathon, and Full Marathon all in 4 days.

Meeting by Chance, Growing by Choice

Jen and Tyrand first crossed paths at the TBOX bar crawl, where they were both part of the "Royal Court." Initially, their connection remained friendly, as they navigated life in Chicago. It wasn’t until a chance downtown encounter led to regular lunch outings that something more began to blossom.

Jen, unsure of whether their friendship had the potential to be something more, took the initiative by setting up what she considers their first date — attending the Aladdin Broadway show. Tyrand, however, claims their first "date" was just another lunch at Billy Goat. Regardless of the timeline, their relationship steadily grew, just like their miles on the pavement.

Running Into a New Passion

While Tyrand had already embraced running after losing a bar bet in 2017 (a shot of malort and an unexpected entry into the Chicago Marathon lottery sealed his fate), Jen’s running journey began during the pandemic. Inspired by Tyrand’s dedication and her own commitment to a postponed Race to Wrigley 5K, she took her first steps with a Couch to 5K program. Encouraged by Tyrand, she joined the CES half-marathon training program in 2021, transforming running from an occasional activity into a true passion.

Training Together, Supporting Each Other

Training for races — whether it’s a first 5K or a World Major — is no small feat. While Tyrand may be the more intrinsically motivated of the two, his consistency and dedication serve as inspiration for Jen. "Honestly, his dedication to training is how he supports me. His commitment is inspiring. Not just to me either, to a lot of people." she notes. In return, Jen is his biggest cheerleader, recognizing when he needs encouragement or when a well-timed rest day is the best strategy.

One of their most cherished moments together was crossing the finish line of the 2022 Chicago Marathon — Jen’s first. Tyrand ran every step with her, ensuring she had the support she needed for all 7+ hours of the journey. More recently, the Dopey Challenge at Disney solidified their bond even further, with Tyrand waiting at mile 25 for Jen, drink in hand, so they could walk the final mile together.

And, of course, we can't forget Tyrand's epic proposal to Jen at the end of the 2024 Dopey Challnege. He managed to get down on one knee after running 48.6 miles in 4 days while sporting his compression socks, sandals, and of course, his Shokz. (If you know Tyrand, you know they are always on him.)

Looking Ahead: Chasing Goals, Together

Both runners have ambitious goals for the future. Jen is currently training for the London Marathon in April, and after plans to focus on improving her speed in the summer through half-marathon training. Tyrand, also training for the London Marathon, with earn his third World Major star in April, and aims to complete all six stars and eventually run races in all 50 states.

Through it all, their shared hobby continues to bring them closer. Whether it's early morning training sessions, destination races, or simply knowing they have someone who understands the highs and lows of training, running has become a cornerstone of their relationship. 

Fleet Feet Training x CES played a pivotal role in their story, not just as a training program but as a community that brought them together. For Jen and Tyrand, running isn't just about the miles — it's about the journey, the memories, and the unwavering support they provide for each other every step of the way.