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 (more on that later), the twosome ran into each other post-filming too.
“My relationship with Kelley has just been a lot of things that have kind of been serendipitous,” Weber said on the “Viall Files” podcast in April 2020. ”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.”
Following their February 2020 reunion, the twosome kept in touch as he navigated his relationships with both winner Hannah Ann Sluss and runner-up Madison Prewett. As viewers may recall, Weber proposed to Sluss during the finale, but their engagement lasted less than two months. The airline pilot later revealed he still had feelings for Prewett, who quit during the finale week. The pair ultimately decided that they were too different to make it work.
Following both breakups, Weber found his way back to Flanagan. Prewett, however, implied that he was still interested in pursuing a relationship with her before he committed to Flanagan.
“He was, like, calling me and texting me being like, ‘I miss you, let’s get back together.’ … He had texted me two days before [he was with Kelley],” Prewett claimed in April 2020. “You were telling me how much you loved me and wanted to get back together and now you’re with the one person that was my best friend. It just feels a little hurtful.”
Us Weekly broke the news in April 2020 that Weber and Flanagan were official. While they announced they were done on New Year’s Eve 2020, there is seemingly more to the story. In fact, the twosome briefly reconnected in early 2021 but their romance fizzled out after Valentine’s Day that February.
In August 2022, the former flames sparked reconciliation rumors after being seen in Chicago together. Us exclusively confirmed the following month that Weber and Flanagan were “full-on back together.”
Scroll through the gallery for their full timeline:
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.” ABC/Maarten de Boer; Chris Pizzello/Invision/AP/Shutterstock
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.” ABC/John Fleenor
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. ABC/Francisco Roman
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.” Shutterstock (2)
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.”
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.” Courtesy Peter Weber/TikTok (2)
Us broke the news that the duo were “fully dating” in late April 2020. “Peter and Kelley are fully dating, but they aren’t admitting it to people,” a source told Us. “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.” Cameo
The twosome seemingly confirmed their romance by sharing a video of them singing Akon‘s “Don’t Matter” on TikTok in May 2020. “Nobody wants to see us together, but it don’t matter, no,” Weber and Flanagan sang in the video. “‘Cause I got you.” Courtesy Peter Weber/TikTok (2)
Weber went Instagram official with Flanagan on May 2, sharing a photo on Instagram that showed them getting close in the cockpit of a small plane. "You caught me," he captioned the shot. "Let the adventure begin." ABC (2)
After a source told Us that the Weber and Flanagan families were both thrilled by the dating news, the lawyer confirmed via Instagram that her mother, Connie Flanagan, “loves” the pilot. Courtesy of Kelley Flanagan/Instagram; Inset: Shutterstock
During their first official interview as a couple, Flanagan and Weber revealed their plans to move to New York City. “We are just really excited for the future,” he told Chris Harrison during the June 8 episode of The Bachelor: The Greatest Seasons — Ever! “When this [pandemic] finally ends, we both have dreams. We’d love to live in New York City for a little bit and get that experience, so hopefully, fingers crossed, that’s in our future. … It’s been great.” The following week, Harrison checked in with Prewett and Sluss. After the host asked both of the women if they would get back together with Weber if he came “crawling back” to them, Flanagan took to her Instagram Stories. “Why are these disrespectful questions still be asked?” she wrote at the time. “The past is the past, let’s let everyone move on in peace.” Courtesy Peter Weber/Instagram
Weber spent time with Flanagan’s family in Illinois in July 2020. “Still missing two of the kids but overall a successful first dinner night! ❤️,” she wrote alongside a photo of her boyfriend with her parents and brothers Jim, Tom and Michael. (Flanagan’s sister, Pamela, and brother John were missing from the get-together.) The pilot later referred to the trip as “the hometown that should’ve been ❤️.” Courtesy Kelley Flanagan/Instagram
"With Kelley, it literally sounds so cliché — I can just be myself. She truly gets me," Weber gushed to Entertainment Tonight in July 2020. "She's my biggest fan and she supports me and she's always there for me. I know I have my partner in crime forever." Weber went on to tell the outlet when he first told Flanagan that he was in love with her. "Neil Lane wasn't there,” he said, referring to the Bachelor’s go-to ring designer. “but I got her this little gumball machine ring. We were having a pool day, and I [sat her on the couch]. … I told her I wanted her to remember this day from this gumball machine ring is the day that I told you that I loved you." Flanagan added that she’s “madly in love” with Weber, but noted that they aren’t in rush to get engaged. "We're not on a reality show anymore, we can take our time," she said. "We don't need to rush anything. We want to make sure each other is in the right headspace, and there's nothing wrong with that. We're happy and we're living life." Courtesy of Kelley Flanagan/Instagram
Weber took part in the latest TikTok trend that uses Taylor Swift’s song “Love Story.” The former Bachelor got down on one knee and fake proposed with a real ring before the camera zoomed out. “Only @kelleyflanagan could ever get me to do this trend…” he wrote. Courtesy Peter Weber/TikTok
“Happy early birthday to the kindest soul on this planet!” Flanagan raved via Instagram while cuddled up to Weber on a rooftop in Chicago. “Love you!” Courtesy of Kelley Flanagan/Instagram
The couple jetted off to Nemacolin Woodlands Resort in Pennsylvania in August 2020 for their first getaway as a couple. “I can’t explain how much fun we had on our first vacation together! Nemacolin is a dream come true and is one of the most amazing places I’ve been in a while!” Flanagan wrote via Instagram. “It will be hard to top but the memories will last forever!” Courtesy Kelley Flanagan/Instagram
“Kelley and Peter are planning to move to New York in January for Peter’s job,” a source exclusively told Us, five months after the couple became Instagram official. “In the meantime, they are looking to get a house in Chicago as an investment. They’re very in love, serious and committed to one another.” Courtesy Peter Weber/Instagram
Flanagan shot down rumors that the pair were engaged in November, telling ET, "We are loving continuing to get to know each other, having lots of great adventures and growing together." Courtesy of Kelley Flanagan/Instagram
Weber called Flanagan his best Christmas present in December 2020 via Instagram after she sported socks with his face on them. Fans later learned, however, that the twosome were on the rocks at the time. “Kelley and I broke up two weeks ago. I flew to Chicago and was finished with the relationship, then my mom really encouraged us to be in the relationship if we wanted to be and to not give up,” he told Entertainment Tonight on January 4, 2021. “Kelley and I operate on two different frequencies, and one isn’t better or worse than the other; we’re just two different people, and those differences surfaced after eight months of dating. But I loved her like crazy, and my mom really cared about her.” Courtesy of Barbara Weber/Instagram
Hours before 2021 began, Weber went public with the split. "While our relationship was filled with countless beautiful memories, our relationship simply didn’t work out in the end," he said in his statement. "Kelley is someone I will always have a special love for." Courtesy of Instagram/Peter Weber
While it didn’t take long for cheating allegations to surface, a source told Us that there was no infidelity involved. “They were together all the time, so there was no way either one could’ve cheated. Their personalities just didn’t mix — that was a big factor for the breakup. They also fought and had many disagreements and didn’t see eye to eye at times,” the source said, adding that Weber pulled the plug. “She could see it coming. He really cared for her and he really loved her.” Courtesy of Barbara Weber/Instagram
Flanagan broke her silence on January 3, 2021. “Peter and I had some unbelievable times together and they will definitely be missed,” the attorney wrote. “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. I’m still hoping to make it to New York one of these days, but for now I just want to focus on my happiness! 2021, I can’t wait to see what you have in store!” Weber left a red heart emoji in the comments section of her post. RB/Bauergriffin.com / MEGA; Courtesy of Kelley Flanagan/Instagram
In February, the pair were spotted partying together in Tampa, Florida, before the Super Bowl. "I’d not seen her since … for a couple of months actually, since things ended,” he later said about their meet up. “But I did see her and it was a good meeting, for sure. We are on good terms, I will tell you guys that." ROGER WONG/INSTARimages.com; Courtesy Kelley Flanagan/Instagram
Flanagan confirmed in March 2021 that following a brief reconciliation and a Valentine’s Day date in New York City, the pair split for good in February. “On my end, there were just a lot of non-negotiables in the relationship that they essentially were seeming to be worked on or saying that they were going to be worked on or changed, and actions kind of speak louder than words,” she said on the “Off the Vine” podcast. “If there is something that I saw as disrespectful in a relationship, I would speak on it and I was pretty vocal. There wasn’t something massive. … Within the relationship, it was fun. It was great, but there was a lot of little things.” Maarten de Boer/ABC; ABC/Randy Holmes
After Flanagan revealed her Lyme disease diagnosis, several of her fellow Bachelor Nation stars reached out to share their support — including Weber. The Illinois native exclusively told Us during New York Fashion Week on September 11 that her ex-boyfriend sent a nice text message indicating that he was sorry to hear about her illness. However, Flanagan explained that she doesn’t text him nor considers him a friend. “It was nice of him, but we went our separate ways and I don’t really have any intention to keep communicating with him or have him in my life,” she told Us at the time. “I wish him the best — I truly do — but again I just don’t really want to be associated, so doing my own thing.” Diana Cooper/Us Weekly
Flanagan slammed Weber, revealing he wasn’t husband material. “Peter and I had a lot of fun, but I don’t know if I looked up to him in the way that I wanted to look up to my spouse,” she said on “Talking It Out” at the time. “I have this with my brothers and my dad, where if I’m in a moment where I need some sound advice and look for who to go to on important decisions, but with Peter, it was just fun and games.” John Salangsang/Shutterstock; Robert O'Neil / SplashNews.com
The pair were seen in Chicago together on August 10. Later that month, he fueled reunion speculation when he agreed with a social media user who said they were having “impure thoughts” about Flanagan. Courtesy of Peter Weber/Instagram
As the twosome declined to comment on their status, they attended Tyler Cameron’s gala for the Andrea Cameron Foundation. Courtesy of Pete/Instagram
Us confirmed on September 26 that the duo were “full-on back together” after sparking romance speculation earlier in the summer. “Peter wants to be in a serious committed relationship and his feelings for Kelley never went away,” a source exclusively told Us, adding, “They're both happy and looking forward to where things go this time around." Shutterstock (2)
Weber and Flanagan attended a Barry’s x Mario Badescu event, where they cuddled up for photos. Courtesy of Mario Badescu
The twosome attended the Global Lyme Alliance Gala together, weeks after Us confirmed their reunion. Courtesy of Peter Weber/Instagram
Flanagan spoke out about her rekindled romance with Weber during an appearance on the “Trading Secrets” podcast, teasing where the couple wanted to live moving forward. “It's a tough one. I love Miami, but it's not feasible for Peter. So yeah, it's been tough,” she told host Jason Tartick, referring to her current home base in Florida. “I mean, I've always been OK with New York. I think New York is amazing, but you know, it's something him and I have to talk about.” The influencer pointed out that New York was the city she likes most of Weber’s possible United Airlines hubs. “We're not necessarily there,” she added. “We have some conversations [to have] when that does happen.” Courtesy of Peter Weber/Instagram
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