Peter Weber and Kelley Flanagan's Full Relationship Timeline (2025)

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.Keep scrolling to see their full relationship 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.”

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.”

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.

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.”

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, Barbara, 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.”

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.”

“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.”

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.”

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."

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.

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.”

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 ❤️.”

"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."

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.

“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!”

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!”

“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.”

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."

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.”

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."

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.”

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.

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."

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.”

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.”

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.

As the twosome declined to comment on their status, they attended Tyler Cameron’s gala for the Andrea Cameron Foundation.

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."

Weber and Flanagan attended a Barry’s x Mario Badescu event, where they cuddled up for photos.

The twosome attended the Global Lyme Alliance Gala together, weeks after Us confirmed their reunion.

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.”

The couple gave their first joint interview since their reunion, telling Us that their relationship is “a lot more relaxed” and “easier” after time away from the series.

“We’re definitely keeping it a little bit more private this time around just because we kind of have that luxury that we didn’t have last time,” Weber said. “And it’s been really, really special. I think we’re both enjoying how it’s been the second time around and things happen for a reason. And I can say I’m very happy.”

Flanagan added: “I’m happy – I genuinely am. We get along, we connect.”

The twosome went on a double date to a New York Jets game with fellow Bachelor Nation couple Victoria Fuller and Greg Grippo.

Weber confirmed at an appearance in Canada that he was single once again. When joking about getting his "legs hair-free" for his "future wife," he quipped, "I've still gotta find her." (Flanagan debuted her relationship with Ari Raptis that June. The pair called it quits in November 2024.)

“I think, honestly, my ex Kelley, we actually kind of admitted we’re like, ‘We were trauma bonded,’” Weber said on “The Ringer Reality TV” podcast. “We definitely fell in love a couple months into dating and all that. We definitely did. It was a really beautiful relationship before it ended.”

Weber and Flanagan reunited to attend the 2025 Coachella music festival together. “Uh oh,” Weber captioned an Instagram Story snap of himself, his ex and a friend riding to the event. The supplement company BelliWelli also caught the pair on camera via a TikTok video in which Weber was offered a sample of their fiber supplement powder.