Peter Weber and Kelley Flanagan’s relationship has been unconventional from the start.
During the January 2020 premiere of season 24 of The Bachelor, fans learned that the attorney ran into the pilot at a hotel in Malibu in August 2019. “Kelley met Peter prior to the taping of the show,” Chris Harrison revealed in January 2020. “This is completely random but they met at a hotel they were both at for separate parties. She knew Peter — Peter obviously didn’t know her — she went up to him, and they met, and they both think this could be destiny.”
While their relationship didn’t work out on the show, the twosome ran into each other post-filming after Weber’s Bachelor relationships with Hannah Ann Sluss and Madison Prewett fell through.
Us Weekly broke the news in April 2020 that Weber and Flanagan were official, but the two later announced their split that New Year’s Eve. The two have rekindled and called things off multiple times in the years since.
August 2019
Prior to filming, Weber and Flanagan randomly crossed paths. She approached him as a future contestant on the show.
A year later, the twosome shared footage of the night they met.
“A year ago today I met this one in a hotel lobby. We danced the night away and then went our separate ways,” Weber wrote alongside clips from the evening. “I truly didn’t know if I’d see her again. This life is beautiful, beautiful. Let’s see what’s next ❤️ @kelleyflanagan.”
September 2019
A month after their run-in, filming for season 24 of The Bachelor was underway — and Weber recognized Flanagan right away. While their relationship got off to a great start, it didn’t last. The lawyer later alleged that ABC producers tried to keep her from Weber.
“[I told him], ‘They don’t let me see you. … You clearly know they push some people forward and they don’t push others forward,’” she recalled in April 2020. “It’s just I saw him, like, things were getting in his head that he wasn’t able to make his own decision and it just kind of pissed me off.”
November 2019
Flanagan was sent packing during week 7 of the season, just before Weber traveled to meet his final four’s families.
“I want someone to be my other half. I want to be with someone and we’re a power couple,” she told Weber on the series. “I want someone to challenge me on a day-to-day basis, and me challenge them, learn from them, and vice versa.”
He proposed to Sluss just before Thanksgiving in November 2019.
February 2020
Days after Weber broke off his engagement to Sluss, he ran into Flanagan at the Super Bowl in Miami. The show was still airing at the time.
“We chat, we end up hanging out and that's when I got her number,” he recalled on the “Viall Files” podcast. “We started to communicate and just stay in touch.”
March 2020
After she was mysteriously left off the list for the Women Tell All reunion in March 2020, Flanagan traveled to Los Angeles when she was invited to the live After the Final Rose taping. While viewers didn’t see Weber or Flanagan interact, she met his mother, BarbaraBarbara, who was clearly a fan.
“She was like, ‘You were my favorite since day one! I love you! You’re beautiful!’” she told Us exclusively in March 2020. “So I guess she was rooting for me. But other than that, she was just the sweetest thing to me so I have no hard feelings toward her. I think she’s great.”
March 2020
Weber and Prewett went their separate ways for good on March 12, 2020, two days after the finale. Less than two weeks later, he was spotted visiting Flanagan in Chicago. “They both appeared to be in a good mood and Peter was even seen dancing a little bit,” an eyewitness told Us at the time.
Prewett later called Weber stepping out with her “best friend” Flanagan on her birthday a “jab” at her.
“I saw something special in Kelley, that’s why she was my best friend. I saw something special in Peter, that’s why I loved him and wanted to fight so hard to make the relationship work. So they’re obviously both incredible and special people,” Prewett said in April 2020, before admitting that she thinks something might have been brewing between the twosome for longer than fans think. “His answers — and her answers — very much contradict the current situation that is happening right now.”
April 2020
Weber and Flanagan spent weeks quarantined together in her Chicago apartment with fellow Bachelorette season 15 alum Dustin Kendrick amid the COVID-19 crisis. While they admitted they were “crushing” on each other at the time, they denied that they were more than friends.
“Are we dating? No. Do I love spending time with her? Absolutely,” Weber said in an April 2020 interview. “Could I see that in the future? Yeah, of course. I’d be extremely lucky and very happy if that happened. Of anyone, I’m the last person that needs to rush into any kind of relationship. I just had an engagement that didn’t work out. I just was trying to pursue things with another woman that didn’t work out. That’s why right now, I’m just taking it really, really slow.”
April 2020
“My relationship with Kelley has just been a lot of things that have kind of been serendipitous,” Weber shared during an episode of the “Viall Files” podcast. “You go all the way back to the very beginning, her and I running into each other before any of this started, her getting a sign of running into me. That was crazy. What I don’t know if a lot of people know is, obviously the show happened, it didn’t work out for us on the show. After the show, I was in Miami, I had the opportunity to go to the Super Bowl there with my brother and I ran into her on Saturday night before the Super Bowl.”
Late that month, Us broke the news that the duo were “fully dating.” A source shared at the time, “Peter and Kelley are fully dating, but they aren’t admitting it to people. She has been much more careful and has been staying in her house ever since her incident with Peter while walking on the Riverwalk in Chicago and doesn’t want to be criticized all over the internet.”
-1743383321-q80.webp "The Valley’s Brittany Cartwright Talks Rift With Katie Maloney and Not Hearing Back From Her, Plus Her Plans for a Breast Reduction")