The connection between Peter Weber and Kelly Flanagan has never been conventional. Fans discovered on the January 2020 season 24 premiere of The Bachelor that the lawyer and pilot met in August 2019 at a hotel in Malibu.
Prior to the show’s taping, Chris Harrison stated in January 2020 that Kelley had met Peter. They happened to run into one other at a hotel where they were both attending separate parties. She approached Peter, who evidently didn’t recognize her, and they struck up a conversation. Both of them believe this might be fate.
Even though their relationship didn’t work out on the program, the two of them kept in touch after filming. On the Viall Files podcast in April 2020, Weber noted, “My connection with Kelley has simply been a lot of things that have kind of been serendipitous.” When all of this began, she and I accidentally bumped into each other, and she showed signs that she was about to hit me.
That was absurd. The show definitely happened, but it didn’t work out for us on the show, which I don’t know if many people are aware of. I met her on Saturday night before the Super Bowl while I was in Miami after the show and had the chance to attend the Super Bowl there with my brother.
The two of them remained in touch after their February 2020 reunion while he negotiated his relationships with both the winner, Hannah Ann Sluss, and the runner-up, Madison Prewett.
They were engaged for less than two months after Weber proposed to Sluss in the finale, as many may remember. Later, the airline pilot admitted that Prewett, who left during the final week, was still on his mind. They ultimately came to the conclusion that they were too different for the relationship to function. Weber found his way back to Flanagan after both breakups. Prewett, however, made it seem as though he was still considering dating her before he decided to marry Flanagan.
He kept saying, “I miss you; let’s get back together,” in calls and texts to me. In April 2020, Prewett stated, “He contacted me two days before [he was with Kelley]. You were confessing your love for me and your desire to reunite, but now you are dating the person who served as my closest friend. Simply said, it hurts a little.
In April 2020, Us Weekly broke the news that Weber and Flanagan were engaged. Even though they stated they would stop on New Year’s Eve 2020, there may be more to the story. The twosome did, in fact, briefly reunite in early 2021, but their romance ended after Valentine’s Day that year. The ex-lovers ignited reconciliation rumors in August 2022 after being spotted together in Chicago.