Peter Weber Challenges Caitlyn Jenner to ‘Double or Nothing’ Golf Rematch After ‘Fun’ Family Outing

Caitlyn Jenner Goes Golfing With Bachelor Peter Weber 2
Peter Weber and Caitlyn Jenner Chris Pizzello/Invision/AP/Shutterstock; MediaPunch/Shutterstock

A reality TV crossover we didn’t see coming. Caitlyn Jenner hit the golf course with Peter Weber and his brother, Jack Weber, and his father, Peter Weber Sr., on Wednesday, June 24.

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“Fun day of golf with the Weber’s,” the 70-year-old I Am Cait alum wrote alongside a selfie with the Bachelor and his family via Instagram. “Wisdom and maturity won over youth and enthusiasm.”

Peter, 28, took to the comments section to demand a rematch.

“Round 2, double or nothing,” he wrote.

Peter’s girlfriend, Kelley Flanagan, and his mom, Barbara Weber, seemingly approve of the foursome, commenting heart emojis on the post.

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Flanagan later revealed in the comments section of The Morning Toast’s Instagram that the Weber family is friends with Caitlyn because “they all love aviation.” Peter also grew up in Westlake Village, California, which isn’t far from the Calabasas neighborhood where the Olympian lived with ex-wife Kris Jenner. The Secrets of My Life author relocated to Malibu after her 2014 split from Kris, 64.

Peter, for his part, is planning to move to New York City with Flanagan, who competed for his heart on the ABC dating series. The season 24 Bachelor and the attorney, 28, started dating in April after they reconnected post-show.

“We are just really excited for the future,” Peter told Chris Harrison via video chat during the June 8 episode of The Bachelor: The Greatest Seasons — Ever!. “When this [pandemic] finally ends, we both have dreams. We’d love to live in New York City for a little bit and get that experience, so hopefully, fingers crossed, that’s in our future. … It’s been great.”

Peter added that he’s “extremely happy” with Flanagan.

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“I remember going in, and I wanted that love story more than anything, and I can honestly say it worked out in the end,” he gushed. “It feels so good to be able to say that and I’m just very hopeful for the future. … I am very, very happy with this one.”

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