Brady Shepherd’s Unlikely Pickleball Finale: Brady Shepherd, a YouTuber known for his comedic and offbeat content, recently brought pickleball into the spotlight during the finale of his self-made dating show series, Trying To Find A Girlfriend. Rather than using dating apps, Shepherd turned his search for love into a full-fledged YouTube reality show, complete with dates, challenges, and even a final weekend where three women lived with him at an Airbnb.
And yes—pickleball made a cameo.
A Reality Show with a Paddle Twist
For the finale, Shepherd took the three remaining contestants to a makeshift pickleball court outside their rental home. It wasn’t your typical pro-style setup. The court had holes, minimal court space behind the baselines, and bushes encroaching from all angles—hardly regulation. Yet, the game went on.
In true reality-TV fashion, the match was uneven from the start. Shepherd brought in a friend and challenged the three women to a three-versus-two game, arguing they had the numbers advantage. But that didn’t help. While Shepherd and his friend were clearly more comfortable swinging a paddle, the women struggled. Most had likely never picked up a racket before.
View this post on Instagram
“Oof. A Swing and a Miss.”
The match quickly became more comedy than competition. The uneven teams, awkward court conditions, and clear mismatch in skills led to chaotic play—and a lot of missed shots. Palm fronds surrounded the court on one side, limiting movement and blocking any chance of a solid return.
As often seen when pickleball pops up on reality TV, this match showcased how not to play the game. But it still made for fun, lighthearted entertainment.
Not Exactly Anna Leigh Waters
Despite the brief dip into pickleball, it was clear athleticism wasn’t the deciding factor for Shepherd. He ultimately chose the least athletic contestant to be his girlfriend. If he were truly scouting for the next Anna Leigh Waters, he might need to rethink his strategy—or just go play at a college court next time.
Still, the segment shows how pickleball continues to pop up in pop culture, even in the most unlikely places—like a YouTube dating show with hidden cameras and DIY rose ceremonies.
News in Brief: Brady Shepherd’s Unlikely Pickleball Finale
YouTuber Brady Shepherd featured a chaotic game of pickleball during the finale of his DIY dating show Trying To Find A Girlfriend. Despite the rough court and messy play, the segment added humor to the show. In the end, Shepherd picked the least athletic contestant to be his new girlfriend.
ALSO READ: Discover the Joy of Pickleball: New Saturday Pickleball Clinic in New Cumberland!