Relive Peter Weber and Kelley Flanagan’s Relationship Timeline From ‘The Bachelor’ to Split to Reunion

Pre-‘Bachelor’

Peter and Kelley “randomly” met a month before filming began in a hotel lobby — this would’ve been around August or September 2019. “I was here in California for one of my best friend’s wedding, and he was there for his 10-year reunion,” the contestant explained on night one. Their unexpected meet-cute was enough to push her to go on the show.
“So, I am going to be honest with you — I didn’t really want to do this at first,” Kelley confessed to the leading man. “I kept saying there would be a sign from God that would tell me I should do this.” The lawyer was just as shook over the circumstances. “That’s insane. I think this is a pretty obvious sign,” she added.

Chemistry From the Beginning

“It was good that he remembered me, and I think the spark is still there, so that’s reassuring that I want to be here,” Kelley gushed after stepping out of the limo. During the first night, Peter also admitted he was “so happy” she was there.

Get It, Girl

Kelley was on the first group date of the season, which took place at an airport. The ladies competed in an obstacle course where Kelley took on Tammy Ly in the final round. The Chicago native ended up winning the challenge and the group date rose.

Lost in the Pack

Kelley went on the pillow fight-themed date during week 3. However, viewers didn’t see much from her amid the drama with contestant Alayah Benavidez.

Yes or No?

The reality babe got her first one-on-one date during week 5 in Costa Rica. She and Peter attend a shaman healing ritual. In a private interview, the pilot admitted that he thought Kelley had been “closed off” during the process. Kelley later said that it wasn’t “easy” giving her “all” on the reality show. 

A Rocky Turn

During the dinner portion of the date, Kelley called Peter out for rewarding the drama in the house. She felt like him pouring energy into the negativity took time away from her and the other contestants. 

What Was *Really* Going On

Kelley opened up about where her head was at during an interview on Ben Higgins and Ashley Iaconetti’s “Almost Famous” podcast on April 7. “I saw that he was getting manipulated every which way, and it just like kind of pissed me off,” she dished. The brunette beauty acknowledged that she could tell his “demeanor” had changed during their one-on-one date.
“Right then and there, I knew something was going on behind the scenes, and I was like, ‘This is bulls—t,’” she continued. “So on our one-on-one, which no one really saw, I just called it out.” Kelley said she confronted Peter about their situation on the show. “I said you clearly know they push some people forward and they don’t push others forward and I was like you’ve been in my position before, what do you want me to do?” Kelley added.

Bye (for Now)

ans said goodbye to Kelley and Natasha Parker during week 7. The lawyer was in the top five but was sent packing in lieu of Hannah Ann and Victoria Fuller during a three-on-one date. With Kelley gone, the final four also consisted of Kelsey Weier and Madison.

November 2019

This is when dates start getting important, so pay attention. Peter got down on one knee and proposed to Hannah Ann in Australia, which concluded filming for season 24. 

January 2020

The season premiered on January 6, 2020 — the leading man and Knoxville native were still together at this point, Hannah Ann revealed during the “Bachelor Happy Hour” podcast with Rachel Lindsay and Becca Kufrin. However, early in the month is when Peter apparently started having doubts and asked his then-fiancée if he could reach out to Hannah Brown.
Hannah Ann and Peter split in mid to late January.

February 2020

Peter attended the Super Bowl with his brother, Jack, on February 2. The pilot revealed he “ran into” Kelley “on the Saturday night before” the big game. 

An Important Detail

Peter said that he got Madison’s phone number during her surprise visit to see him after filming wrapped. The Alabama native was seen filming with the show in her hometown on February 11, in photos obtained by Reality Steve, so it’s safe to say her reunion with Peter happened shortly after. 

March 2020

Peter and Madi reunite again during After the Final Rose on March 10. “I didn’t physically see her until [we were] on stage. But we were able to talk and have some honest, good conversations. Yeah, conversations we should’ve had when we were dating on the show,” the reality stud explained on “The Viall Files” podcast. “Looking back on it, I feel like we should’ve tried to see each other before we showed up on stage together.”

Where They Left Off

The leading man and runner-up said they were taking things “one day at a time” on After the Final Rose, but they announced their “mutual” decision to go their separate ways for good three days later.
“She came over to my hotel … that was mainly just [us] trying to be there for each other. The second day [two days following ATFR] was when we pretty much spent the entire day together, that was… OK, let’s figure this out,” recounted Peter on Nick’s podcast. “I remember going to her hotel … it was super sad. For probably six hours, we stayed on her bed there, we laughed, we cried, we hugged each other … it was rough.”

Cue Kelley 

During the April 7 podcast, Peter explained that he reconnected with Kelley “a couple of weeks ago.” Although it’s unclear when the exes crossed paths, the Chicago lawyer was in Los Angeles for ATFR, so it’s possible they saw each other the weekend following the dramatic live show.
“I’m out with Dylan [Barbour] and Devin [Harris] and I was texting Kristian [Haggerty], asking her if she wanted to come out with us. She comes out with us, she’s with Kelley. Me not knowing this. They show up, I see Kelley again … jaw drops,” Peter said. “We chat, we end up hanging out and that’s when I got her number. We started to communicate and just stay in touch.”

Understanding

“I think that this whole process maybe got to him a little bit,” Kelley exclusively told Life & Style about Peter’s confusion during and after the season on March 12. She added that he “needs to figure out his own stuff.”

Quarantine Crew

On March 25, Peter and Kelley were photographed in Chicago together with fellow show alum Dustin Kendrick. Through various TikTok videos and social media posts, it became clear that the California resident is staying with Kelley amid the coronavirus pandemic. 

A Little Clarity

In early April, the former flames were “going slow” with their romance. “Are we dating? No,” Peter divulged on Nick’s podcast. “Do I love spending time with her? Absolutely. We’re not dating. Could I see that in the future? Yeah, of course. I’d be extremely lucky and very happy if that happened.”
He also admitted he was “crushing on Kelley” during Kaitlyn Bristowe’s “Off the Vine” podcast on April 7. 

Officially Official

A source told Us Weekly Peter and Kelley were “fully dating” at the end of April, and the pilot confirmed it himself on May 2. “You caught me. Let the adventure begin,” he captioned a photo of the two kissing in an airplane.

Going Strong

The pair spent the summer having a blast together and have even been spending time with Peter’s family at his home in California. 

Big Plans

The next step! Peter and Kelley revealed in July they plan on moving to New York City together. The lawyer will continue to work remotely from her Chicago-based law firm while the reality stud’s career as a pilot allows him to live anywhere.

“I’m super excited to take this next step with Kell and move to New York and to see what adventures await,” the pilot said during an interview with Entertainment Tonight.

Kelley updated fans on their plans on September 16 and said they postponed the move until January 2021 amid the coronavirus pandemic.

Head Over Heels

Peter’s mom exclusively told Life & Style the reality couple is “madly in love” with each other. “They’re very compatible. The most important [thing] I think in any relationship is to really have fun with each other — and they definitely do have fun with each other!” Barb dished in July 2020.

First Trip Together

“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!” Kelley gushed via Instagram on August 28 about the Pennsylvania resort. “It will be hard to top but the memories will last forever!”

Big Apple, Here They Come!

In December 2020, Peter confirmed her and Kelley are moving to New York City in “early January” 2021.

It’s Over

Peter revealed via Instagram in late December that he and Kelley had split. “Love is a funny thing. It can make you feel on top of the world and it can make you feel a pain you wish didn’t exist. I’m here to share that Kelley and I have decided to go our separate ways. While our relationship was filled with countless beautiful memories, our relationship simply didn’t work out in the end,” he wrote. “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.”

Barb Weighs In

Peter’s mom shared her thoughts on the split in a comment on her son’s Instagram reveal post. “Love can be fickle and it is not for the timid,” the 63-year-old wrote. “Those who have experienced it know this all too well. But it is better to have loved and lost than never to have loved at all. Our hearts ache for you two. Kelley will always have a piece of our hearts and we wish her only the best. Mom and Dad.”

Moving On … In the Same State

Although they split, Peter revealed on January 8, 2021, he was still moving to NYC solo. “It is officially moving day. I’ve got all this stuff packed up right here ready to go. New York, we comin’!” he said on his Instagram Story.

On January 10, Kelley announced on Instagram that she is also making her way to the Big Apple but is waiting until March. “I’m excited to share my next chapter with you guys, and I’ll try to be as open as I can knowing that I will hit struggles along the way,” the lawyer wrote. “In the meantime, I am trying to figure out my future living situation in New York (searching for a roommate and apartment), spending time with my friends and family and focusing on my career!”

Bachelorette?

In January 2021, Kelley revealed during a True or False game on her Instagram Stories that she would “definitely consider it” if she was approached to star as the Bachelorette in the future. Hmm …

Back On or Amicable Exes?

Peter and Kelley sparked reconciliation rumors when they were spotted around Tampa, Florida, together during Super Bowl LV. Photos and videos from several Bachelor fan accounts showed the former couple at a nightclub and hanging out poolside. They did not respond to speculation by the time of publication.

Peter Explains …

The pilot gave a little insight into where he and Kelley stand now after reconnecting during the weekend of Super Bowl LV in Tampa.

“I’d not seen her since … for a couple of months actually, since things ended,” he explained during a Zoom call with fans on February 13, which was later shared on TikTok. “But I did see her and it was a good meeting, for sure. We are on good terms, I will tell you guys that.”

Out and About Again?

Both Kelley and Peter shared Instagram Stories from Good Bar in NYC around the same time on February 16. The former flames appeared to be hanging out with fellow Bachelor Nation alum Dustin Kendrick.

Back Together!

Peter and Kelley decided to give their romance another go 21 months after they split. They are “full-on back together,” Us Weekly reported on Monday, September 26. The couple “rekindled their romance this summer and have been spending a lot of time together since then,” the insider said, as the pair have been having “a lot of fun together” after reconnecting.

“Peter wants to be in a serious committed relationship and his feelings for Kelley never went away,” the source continued, adding, “They’re both happy and looking forward to where things go this time around.” The news came five days after the two were caught on video having a sexy dance together at a black-tie gala in Florida.