It’s the question Bachelor Nation has been asking: How did Caitlyn Jenner and Peter Weber meet?! The I Am Cait alum and the season 24 Bachelor went viral on Wednesday, June 24, when Caitlyn posted an Instagram photo of of her, Peter and the pilot’s younger brother, Jack Weber, at a golf course.
In the picture, Peter, Jack and a friend could be smiling next to and behind Caitlyn, as the Keeping Up With the Kardashians star held up a one dollar bill. “Fun day of golf with the Weber’s. Wisdom and maturity won over youth and enthusiasm,” the Olympian wrote in the caption.
As expected, the photo led to many questions from fans. Most common was how do Peter and Caitlyn even know each other?! While the two have been silent on their friendship since Caitlyn posted her Instagram photo, Peter’s girlfriend, Kelley Flanagan, who competed on his season of The Bachelor in 2020, revealed in a comment on The Morning Toast’s Instagram that Pilot Pete and the athlete seemed to have met and became friends because of their love of planes.
As we all know, Peter, also known as Pilot Pete, is a pilot for Delta Air Lines. Peter’s brother, Jack, is also a pilot. “Are they friends?” a fan commented on The Morning Toast’s regram of Caitlyn’s photo. Kelley responded, “Lol. They are! They all love aviation!” She also included a plane emoji for good measure.
As for Kelley and Peter, the two confirmed their relationship in May with an Instagram photo of them kissing in a plane. Kelley was eliminated in the final five of Peter’s season before Hometown Dates. Peter went on to propose to Hannah Ann Sluss before he broke up with her to pursue a relationship with his runner-up, Madison Prewett. Days after Peter and Madison made their relationship official on After the Final Rose, the couple split. Weeks later, Peter and Kelley sparked romance rumors when he was photographed in Chicago with her and the two posted TikToks together. Now, it seems they’re full-on hanging out with Caitlyn Jenner.