Caliph and Carolyn's friendship began in 2018 through their shared participation in the Major Taylor Cycling Club of Chicago. Their bond deepened significantly during the COVID-19 pandemic, as they relied on each other for support amidst the uncertainty and isolation. Their love for one another grew quickly as they endured through those challenging times. The empty roads of Northwest Indiana became their refuge, with countless bike rides providing a backdrop for shared conversations and mutual encouragement. They eventially moved from MTCC to the Misfits Cycling Club of Chicago and continue to ride with them to this day.

Caliph and Carolyn eventually bought their first home near their cycling route for easy access. You can often find them riding into Indiana if they are not visiting family in Tennessee.

Their shared experiences extended beyond cycling; in 2021, they began attending Anthem Church in Hammond, further strengthening their connection through shared faith and community involvement. They officially joined Anthem in 2023. Even as life returned to a more familiar rhythm, their friendship, forged in challenging times, remained a constant. Caliph and Carolyn also have enjoyed trips to Canada and Mexico throughout the years together. They continue to cycle together, celebrating their resilience and the enduring power of their bond.