Kelley Flanagan and Peter Weber's Relationship Timeline

From The Bachelor to their acrimonious breakup and reconciliation, here's a look at Peter Weber and Kelly Flanagan's relationship

Kelley Flanagan, Peter Weber
Peter Weber; Kelley Flanagan. Photo: Presley Ann/Getty Images; Aaron Poole/E! Entertainment

Peter Weber and Kelley Flanagan are back together again.

Weber's 2020 season of The Bachelor was a wild ride, ending in a broken engagement with Hannah Ann Sluss, a rekindling of Peter's relationship with runner-up Madison Prewett and then their break-up days later. Who would've thought after the cameras stopped rolling there would be even more to unpack?

In 2020, Weber a.k.a. "Pilot Pete" started dating Flanagan, who was eliminated before hometown visits. After becoming Instagram official, it seemed like the two made a safe landing in the middle of a worldwide pandemic; however, Flanagan and Weber split for the first time before New Year's Eve and, after a brief reunion, separated again after Valentine's Day 2021.

In October 2022, however, Weber and Flanagan shocked fans when they announced they were back together yet again. "Who would've thought, cuz not me 🥰," Flanagan captioned a photo of her and the former Bachelor at the Empire State Building shortly after the pair confirmed they had reunited.

From their chance encounter at a hotel to their breakup and eventual reconciliation, here's a look at Peter Weber and Kelly Flanagan's relationship timeline.

August 2019: Kelley Flanagan and Peter Weber have a chance encounter

John Fleenor/ABC

Before we jump into their current history, it should be noted that the pair actually met before filming on Peter's season even started.

According to Flanagan, she had been weighing whether to go on the reality series while at a friend's wedding when she spotted Peter himself at the same hotel for his 10-year high school reunion. She approached him, and there was a spark — so she signed up.

"I didn't really want to do this at first. I kept saying there would be a sign from God to tell me if I should do this," she told Peter.

Doesn't it make their current relationship seem sort of serendipitous?

Fall 2019: Kelley Flanagan competes for Peter Weber's love

One month after they first meet, Kelley began competing for Peter's heart, but that journey wasn't an easy one.

In April 2020, she opened up to Bachelor Nation alumni Ashely Iaconetti and Ben Higgins, explaining that it was producers that kept the pair from getting to know each other.

While appearing on the Almost Famous podcast, the lawyer explained that everything is not as it seems in the Bachelor mansion.

"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 a hundred percent that like producers were in his head," she said on the April 7 pod episode. "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.' "

She also told the hosts that she had a moment to talk to Peter while the cameras weren't rolling. She explained, "[I told him], 'They don't let me see you. They locked me up in a closet for three hours last week, and they won't let me see you.' I said, 'You clearly know they push some people forward and they don't push others forward.' … 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."

Her declaration wasn't enough to save her from being eliminated from the competition: she was sent home before hometowns.

March 10, 2020: Kelley Flanagan attends After the Final Rose with Peter Weber

Kelly was in the audience for the After the Final Rose finale but not the Women Tell All, which made fans a little suspicious of her relationship status.

During the show, Kelley watched as Peter broke off his engagement with Hannah Ann, got back together with Madison and had an awkward confrontation with his mom, Barb. Through it all, not even a little peep!

March 11, 2020: Peter Weber's mother weighs in on Kelley Flanagan

But Peter's mom still had things to say! Barb hopped into the comments of Kelley's Instagram to call her "The Most Beautiful, Elegant, Classy, Intelligent Stylish Girl in the world!!!!" (Keep in mind, her son was still technically dating Madison at this time.)

March 12, 2020: Kelley Flanagan shuts down rumors about her and Peter Weber

Kelley Flanagan, Peter Weber
John Fleenor via Getty; Eric McCandless via Getty

The lawyer shut down rumors that the pair were together (and that she was pregnant with his child).

She told E! News, "I have heard that. I heard that I'm pregnant and I also heard that I'm with Peter right now. I'm not with Peter. I promise I'm not dating Peter. I'm not dating Peter."

March 23, 2020: Kelley Flanagan and Peter Weber are spotted in Chicago

Despite the stay-at-home order in place in Illinois at the time, the pair were spotted goofing around on the Chicago River Walk with Dustin Kendrick, who competed in Hannah Brown's season of The Bachelorette.

April 12, 2020: Kelley Flanagan and Peter Weber create TikTok videos together

Around this time, the former Bachelor started to make TikTok videos (weren't we all at this point in quarantine) and it was clear that he was quarantining with Flanagan. He even tagged her in a video of himself reading mean comments on another one of his videos.

She started making appearances in his videos (along with Dustin Kendrick). The trio did the "Flip the Switch" challenge, and a few funny lip-sync videos. Kelley even showed up in one of Peter's Cameo videos.

Peter Weber and Kelley Flanagan

Peter explained to fellow Bachelor alumnus Nick Viall how exactly their social distancing arrangement came to be.

"She's always been supportive of me," he said in early April, according to E! News. "Long story short, I wasn't working so I thought I'd go out [to Chicago] and spend some time with her, take her mind off some [family] things. This was right when everything was starting to hit with the quarantine stuff … and it kind of just became a thing where we've always gotten along really well, and had really good chemistry. We just enjoy each other's company."

At the time, Weber denied that he and Flanagan were together.

"Are we dating? No. Do I love spending time with her? Absolutely," he said. "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. 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."

He did admit, however, to Kaitlyn Bristowe on her Off the Vine podcast, that he was "crushing on Kelley."

"We have just been enjoying each other's time and company, I love being around her," he said. "She's been so amazing, so patient with me. It's exactly … what I needed in this kind of situation and I'm so grateful for her."

Weber also appeared on Rachel Lindsay and Becca Kufrin's Bachelor Happy Hour podcast, where the hosts pressed him for all of the inside info about their relationship.

"You said you're taking it slow and you're not dating, yet you literally called where you are 'home' right now," Lindsay said. "You said, 'I'm just making this my home base.' That kind of sounds fast, to see each other every day. How many bedrooms does Kelley have?"

"We're in quarantine together!" Weber said with a laugh. "She's got three bedrooms … we each have our own room. And we've got Sophie here too, Dustin's dog, so we're having a party. It's a good time."

April 28, 2020: Kelley Flanagan and Peter Weber are officially a couple

Peter Weber, Kelley Flanigan
Kelley Flanagan and Peter Weber. Peter Weber/instagram

A source told PEOPLE that the pair were dating and officially "a couple." Days later, they seemed to confirm the news themselves with — you guessed it — a TikTok.

In the video, the pair sang along to Akon's timeless hit "Don't Matter" on Weber's TikTok. The former Bachelor also reposted the clip on his Instagram Story.

May 2, 2020: Peter Weber's family makes his relationship with Kelley Flanagan official

First, Peter took to Instagram to post a photo of him and Kelley kissing while he flies a plane with the caption, "You caught me. Let the adventures begin."

Then, Peter's mom, Barb, created a collage of photos of her son with his new girlfriend and captioned it simply, "Serendipity." Looks like she already approves of Kelley more than she did Peter's ex, Madison.

Peter's dad posted his own photos of the pair and wrote, "Happiness is finding your copilot."

May 12, 2020: Kelley Flanagan and Peter Weber ride a tandem bicycle

The couple eventually made their way back to California, where Weber's family lives, to social distance there. They were spotted on May 12 riding a tandem bicycle and it looks like a very fun one-on-one date, if you ask us!

Bachelor Peter Weber Rides A Tandem Bike With His Co-pilot Kelley Flanagan In Los Angeles, California

Kelley also posted a photo of Peter to her Instagram and joked in the caption, "I know I'm a handful.. good thing you have two hands 😜😘."

Looks like Pilot Pete has finally found his co-pilot.

May 25, 2020: Peter Weber calls Kelley Flanagan his “little ray of sunshine”

Weber and Flanagan continued to play their relationship out on Instagram when Weber posted a photo of a kiss with Flanagan. In the caption, he wrote, "My little ray of sunshine."

July 14, 2020: Peter Weber says he is "super excited" to move to N.Y.C. with Kelley Flanagan

Weber told Entertainment Tonight that he would be moving to N.Y.C. with Flanagan later in 2020, and he was "super excited" about the move "to see what adventures await."

However, despite their plans to move in together, Weber said at the time they weren't in a "rush."

August 4, 2020: Peter Weber celebrates his birthday with Kelley Flanagan

Peter Weber, Kelley Flanagan
Kelley Flanagan/Instagram

Weber celebrated his 29th birthday with Flanagan and his family and friends with a balloon-filled backyard party. Flanagan marked the occasion with an Instagram post of several photos of the duo together with the caption, "Happy early birthday to the kindest soul on this planet! Love you!"

Later, Weber showed Flanagan in his Instagram Story with the caption, "Best present ever right here."

August 18, 2020: Peter Weber shares memories of meeting Kelley Flanagan one year ago

One year after meeting Flanagan at a hotel — just a month before cameras rolled on The Bachelor — Weber marked the anniversary of their meeting with an Instagram post in tribute to his girlfriend.

"We danced the night away and then went our separate ways," Weber wrote as a caption with videos of the two from that fateful evening. "I truly didn't know if I'd see her again. This life is beautiful, beautiful. Let's see what's next ❤️ @kelleyflanagan."

December 31, 2020: Peter Weber and Kelley Flanagan break up

On New Year's Eve, Weber announced on Instagram that he and Flanagan had broken up.

"Love is a funny thing," Weber wrote in the post. "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."

Weber also said he has "countless beautiful memories" of the relationship, but that it "simply didn't work out in the end." The couple had not moved together to N.Y.C. as Weber said they would earlier in the year, and in early January, Weber moved to the Big Apple without her.

On Jan. 3, Flanagan shared her own Instagram post about the split, noting, "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."

March 16, 2021: Kelley Flanagan and Peter Weber briefly reunite before calling it quits (again)

For her first-ever podcast interview, Kelley Flanagan appeared on Kaitlyn Bristowe's podcast, Off the Vine. Flanagan revealed she and Weber had rekindled their romance shortly after the New Year but broke up again in February 2021 after Valentine's Day.

"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," Flanagan told Bristowe.

Flanagan also shared that she asked Weber not to post about their initial breakup on New Year's Eve so she could share the news with her family and friends, but he did so anyway because he felt he had to do it before the new year.

On May 21, Flanagan appeared on another podcast, Chicks in the Office, and revealed that the couple's final split was ugly. "It ended really badly," she said. "I essentially went off on him. I ended up leaving New York and going to one of my girlfriend's houses and hanging out with her. He texted me. I didn't respond and then found some news out that I wasn't happy about. We still had each other on Find My Friends, we were closing it out, it was ending but still wasn't necessarily done." Flanagan said she eventually told Weber to "get the hell out" of her life and lose her number.

On May 26, Weber said on his podcast, Bachelors in the City, that he has "100 percent moved on" from Flanagan and that they weren't "right for each other."

September 22, 2022: Kelley Flanagan and Peter Weber dance together at a Florida gala

Weber and Flanagan attended the Andrea C. Cameron Foundation's annual gala where they were seen showing off their dance moves, spinning and smiling on the dance floor. Flanagan wore a red dress with a one-shoulder neckline while Weber dressed in a white dress shirt and bow tie.

Flanagan commemorated the night by posting a group photo on Instagram. In the snap, Flanagan and Weber stood together with their arms around each other's waists. "Such a fun night celebrating the @andreaccameronfoundation," she wrote in the caption.

October 14, 2022: Kelley Flanagan and Peter Weber confirm they're back together

Third time's the charm! Flanagan and Weber have made their relationship Instagram official (again).

The pilot posted a photo of him cradling Flanagan in his arms at Yankee Stadium. "Home Run," he captioned the image.

Shortly after, Flanagan reciprocated with her own post — a photo of the couple at the Empire State Building.

"Who would've thought, cuz not me 🥰," Flanagan wrote, as Weber teased in the comments section: "Does this mean I get a follow back now? 😘."

October 29, 2022: Peter Weber teases Kelley Flanagan for attending Madison Prewett's wedding solo

Flanagan flew solo for Prewett's wedding in Dallas, Texas, despite having rekindled her romance with Weber.

The former Bachelor contestant, who donned a stunning green gown, posted a photo from the wedding on Instagram, and Weber had just one question: "Where's peter."

After a little back-and-forth banter, that included Flanagan telling Weber to "get to bed," he ended the conversation in the comments with "you look beautiful."

November 8, 2022: Kelley Flanagan shares footage from a romantic cruise with Peter Weber

Flanagan shared a glimpse of her romantic cruise with Weber in a TikTok video. "I had no idea cruise ships looked like this these days," she said in a voiceover, as a clip of the pair's living room was shown.

The Bachelor alum also listed the ship's fun amenities, saying, "We had our own private hot tub and the bedroom was upstairs. It is just absolutely breathtaking. Everything was amazing," she added, showing off the bar and casino.

January 10, 2023: Kelley Flanagan and Peter Weber attend Plane movie premiere in New York City

Flanagan and Weber walked the red carpet together — and even snapped a photo with the film's star, Gerard Butler. The Bachelor alum wore a beaded gown by Alamour, while Weber looked dapper in his signature blue suit.

"Such a fun date night seeing @planemovie!" Flanagan wrote on Instagram. "If you heard the loudest scream in the theater, I apologize… My adrenaline was extremely high the whole movie!"

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