Peter Weber went on a golf outing with a surprising celebrity friend: Caitlyn Jenner. The Bachelor star and his family spent a day on the golf course with the 1976 Olympic gold medalist and was all smiles — even after losing to the former Keeping Up with the Kardashians star.
Caitlyn, 70, took to Instagram to share a photo of herself with the most recent The Bachelor star, his brother Jack Weber, and the duo’s dad, Peter Weber Sr. In the caption of the post, Jenner boasted that “wisdom and maturity” won the game over “youth and enthusiasm.” The former Olympian also held up a $1 bill in the picture as proof of her win, with the elder Weber as her golf partner.
In the comments to the post, Peter Jr., whose tumultuous The Bachelor season aired on ABC earlier this year, revealed that he wants another chance to beat the legendary Olympic athlete on the golf course.
“Round 2, double or nothing,” Pilot Pete wrote in the comments section.
His brother Jack also called for a rematch, while family matriarch Barb Weber and The Bachelor star’s girlfriend Kelley Flanagan posted heart emoji.
Other commenters marveled over the reality TV crossover they never saw coming.
“Wait what lol,” one fan wrote. “Caitlyn & Pilot Pete?”
“When worlds collide,” added another.
“Crossover of the century,” a third fan chimed in.
“The crossover event we never knew we needed,” a fourth remarked.
It is unclear how the Webers know Jenner. But The Bachelor fans know that Caitlyn’s ex, Kris Jenner, is a superfan of the ABC dating franchise and even appeared on the aftershow Bachelor Live back in 2016.
Earlier this year, the Instagram site It’s The Snatchelor also shared a video of a celebrity party in which The Bachelor star appears to be in the background. The caption to the post, which can be seen here, teased that Peter was at a party with Caitlyn’s daughter, Kylie Jenner, and that he can be heard talking about Kelley in the party video.
It is also known that Peter Jr. grew up in the Los Angeles area and has several known celebrity friends. Both Bella Thorne and Victoria Justice have described the Delta Airlines pilot as a longtime family friend, according to People.
The new photo of Pilot Pete’s and the Jenner patriarch comes a few months after his The Bachelor ex, Madison Prewett, was caught on video while shopping at Target with pop superstar Selena Gomez and then playing board games with the singer and her friends.