The season 24 Bachelor met the Chicago-based attorney shortly before filming for his season of the ABC series began in September 2019. After hitting it off during their brief encounter, Flanagan was one of the contestants competing for the pilot’s heart. In the end, she was sent home before the hometown dates. Both Weber and Flanagan have suggested that she wasn’t given a fair shot with production.
“The first couple of weeks I saw him look at me differently compared to when we got on our one-on-one and I could tell 100 percent that like producers were in his head,” she said on the “Almost Famous” podcast in April 2020. “Because on the one-on-one, nothing happened between us but he had this, like, demeanor toward me that was so pissed off and I was looking at him, like, ‘What the hell were you told?’ because nothing happened here for you to have this attitude. And so right then and there, I knew something was going on behind the scenes, and I was like, ‘This is bulls–t’. … Things were getting in his head that he wasn’t able to make his own decision and it just kind of pissed me off.”
During an appearance on Us Weekly’s “Here for the Right Reasons” podcast in April 2021, Weber acknowledged that he started “getting less and less and less” time with her on the show.
“On our one-on-one in Costa Rica, we had, like, two seconds of off-camera time, off-mic time. We were walking in this hot tub, like, in this waterfall thing and I had heard that she wasn’t necessarily cooperating the best with production and I’m like, ‘Listen, just trust me to do what they’re saying, like, I want to see more and want to spend more time with you and they’re not letting that happen. So you just got to make them happy so you know we can give this a shot,'” he said. “I don’t think she got the fairest chance or whatnot on the show if I’m being honest. And I think production would say the exact same thing.”
Despite not ending up together on the series — he proposed to Hannah Ann Sluss during the finale but broke things off while the show was airing because he had unresolved feelings for runner-up Madison Prewett — Weber and Flanagan reconnected post-show and started dating in April 2020.
After announcing plans to move to New York City together in early 2021, Weber revealed on New Year’s Eve that the duo split.
“I’m here to share that Kelley and I have decided to go our separate ways,” he wrote in December 2020. “While our relationship was filled with countless beautiful memories, our relationship simply didn’t work out in the end. 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. Thank you Kelley.”
Flanagan waited four days to address the split (keep scrolling for why).
“It saddens me to say this but Peter and I have decided to go our separate ways,” she wrote in January 2021. “Peter and I had some unbelievable times together and they will definitely be missed. Unfortunately him and I are in two different stages of our lives and saw our future paths differently. I wish Peter the absolute best and want to thank everyone for your continued support as I move on to my next chapter.”
The twosome went on to briefly reunite before making headlines for the messy back-and-forth about their breakup. Scroll through for a breakdown of their different sides of the story: