Peter Weber Admits to ‘Self-Sabotage’ in Relationships: I’m a ‘Hopeless Romantic’ With High Expectations

Blaming himself. Peter Weber has been doing some soul-searching this year, and he thinks he knows why he’s been so unlucky in love.

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“I feel like, sometimes, the hopeless romantic in me kind of backfires, because I put such this high level of expectation in my head,” the former Bachelor, 30, said during the Tuesday, August 24, episode of his “Bachelors in the City” podcast. “And so I’ve been really kind of — in these last eight, nine months — really just realizing that and observing how I have been in the past and how I want to try to change myself in the future, moving forward.”

Peter Weber Achilles Heel Dating Is Being Hopeless Romantic
Peter Weber at the ABC TCA Winter Press Tour in Los Angeles on January 8, 2020. Kathy Hutchins/Shutterstock

The California native has been single since his December 2020 split from Kelley Flanagan, except for their brief reconciliation in February. The pilot admitted on Tuesday’s podcast that the past nine months mark the longest stretch of his dating life that he’s been single.

Weber added that his high expectations have caused relationships to end earlier than they otherwise would.

“I think that’s probably my biggest Achilles heel is, honestly, the hopeless romantic,” he explained. “It starts off great, it starts off very passionate, a lot of fire, and I’m all about that. … If I’m being completely honest with you guys, I feel like maybe I self-sabotage relationships.”

Weber and Flanagan, 29, met shortly before season 24 of The Bachelor began filming in fall 2019. The attorney was one of the contestants on the show, but she finished as the fifth runner-up. During the season finale, Weber proposed to Hannah Ann Sluss, but they broke up shortly after filming wrapped. He later dated runner-up Madison Prewett, but they called it quits in March 2020.

Peter Weber and Kelley Flanagan's Relationship Timeline

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The following month, Us Weekly confirmed that Weber and Flanagan had reconnected and started dating. Eight months later, however, the pilot announced that the pair had decided to go their separate ways.

“While our relationship was filled with countless beautiful memories, our relationship simply didn’t work out in the end,” he wrote via Instagram on New Year’s Eve. “Kelley is someone I will always have a special love for. Someone I have learned more from than she will ever understand. Someone I am so thankful came into my life and someone who I will always wish all of life’s greatest blessings on. These moments in life always hurt, but in my opinion that shows you it was worth the time you spent together.”

Peter Weber vs. Kelley Flanagan: Everything They’ve Said About Their Split

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The pair’s post-breakup relationship has been tumultuous, with Flanagan claiming in May that their romance ended “really badly.” Weber responded to her claim with an accusation of his own, saying in an episode of his podcast that he thought her comments were “very calculated.”

Earlier this month, however, the Bachelorette alum said they’d worked hard to put the past behind them.

“Listen, obviously there’s two sides to every story, and yes, it’s true that usually the truth lies a little bit, you know, in between both those sides,” he said during an episode of the “Tea With Publyssity” podcast. “But I said my piece, and, like, I have no desire to further that. … I’ve moved on. I know she’s moved on.”

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