‘Bachelor’ Peter Weber and Kelley Flanagan’s Relationship Timeline


Remember back in February 2020 when Peter Weber’s season of The Bachelor first aired? I believe that was approximately 10 years ago? Yeah, well, he’s still out here having the ~most dramatic season ever~, and his time on Bach ended literal months years ago. As a reminder, Peter got engaged to Hannah Ann Sluss:

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Then he dramatically broke up with her:

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And then he got back together with Madison Prewett:

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Only to break up with her, like, two days later:

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You’d think Peter would want to take a break from romance after ending two relationships back to back, but apparently not, because he spent 2020 dating Kelley Flanagan…until they broke up on New Year’s Eve….and then (maybe) got back together again. It’s truly been a journey, so let’s start with what went down on the “Women Tell All” special…

February 25, 2020

Kelley posts this photo, proving that she was in Los Angeles during the “Women Tell All” taping. This will become important in a moment!

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Meanwhile, the internet realizes that every single member of Peter’s family is following Kelley on Instagram.

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Instagram

March 2, 2020

The “Women Tell All” airs and fans immediately notice that Kelley is missing. Which seems extremely weird considering she was in L.A. during the taping? If you were lurking on Bachelor fan accounts around this time, you probably recall people being convinced that Peter and Kelley were secretly hooking up and speculating that producers didn’t want her in the audience because it’d give away the ending.

March 10, 2020

The live “After the Final Rose” special airs on ABC and, for some reason, Kelley is in the audience. Bachelor Nation remains convinced something freakin’ weird is up.

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March 11, 2020

Peter’s mom Barb slides into Kelley’s Instagram comments to make it CRYSTAL CLEAR who she wants her son to be with (reminder: at this time, he’s fully dating Madison). Barb straight-up calls Kelley “The Most Beautiful, Elegant, Classy, Intelligent Stylish Girl in the world!!!!”

I’m truly lol.

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Instagram

March 12, 2020

Reality Steve addresses rumors that Kelley and Peter are hooking up:

“Let’s just say ever since Super Bowl weekend (just days after he ended his engagement to Hannah Ann), there have been rumors swirling Peter spent the weekend with Kelley. I don’t know if we can rule those out anymore.”

Meanwhile, Kelley shuts down said rumors to E! News, saying:

“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 25, 2020

Photos drop (and are then deleted) of Kelley and Peter hanging out in Chicago while everyone is supposed to be social distancing (ugh, guys). He’s caught twirling her over his shoulder, and naturally, Bachelor Nation loses it (including Hannah Ann, who promptly deletes all her IG photos of Peter).

April 2, 2020

Okay, a LOT goes down on this fated day. Not only do fans figure out that Peter has been posting TikToks from Kelley’s house based on the freakin’ rug he’s standing on:

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Instagram

He goes ahead and tags her in this Insta video:

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And on top of that, fellow Bachelor Nation star Clay Harbor (who chilled with Peter and Kelley in Chicago) blows up their spot during Instagram Live, straight-up saying “yes” when asked if they are dating:

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April 7, 2020

Peter gives an update on his relationship status with Kelley—FINALLY—during his time on Nick Viall’s Viall Files podcast, saying:

“Are we dating? No. 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. 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.”

(Save this tidbit for later, folks.)

April 28, 2020

An Us Weekly source confirms that Peter and Kelley are dating—*sarcastic voice* surprise, surprise. According to their insider, “Peter and Kelley are fully dating, but they aren’t admitting it to people.” The source adds that Kelley “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.” Interesting!

May 3, 2020

Aaaaaaand the moment you’ve all been waiting for! Peter and Kelley finally put us all out of our misery by making their relationship Instagram official.

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May 20, 2020

Peter’s fully out here selling tea for money on Cameo, but I can’t even get mad at it because he spills why he ultimately chose to be in a relationship with Kelley:

“You guys want some inside scoop here on why I ultimately picked Kelley? All right, here’s what I can do. To be completely honest, I think just the nature of the show definitely works and I’ve said that since day one. I still believe it works, but I think specifically for the type of relationship between, you know, Kelley and myself just wasn’t the most organic type of situation for us if it was going to actually work. And that’s okay, that’s totally okay because each relationship is different.

What’s meant for you and what’s yours will always be yours, and nothing can ever change that. So obviously, we’ll see what the future holds for Kelley and I, but I think it’s a beautiful story, definitely a beautiful love story of what’s yours is yours and it will always come back to you, no matter what….That’s kind of always been our relationship. We’ve kept coming back in each other’s lives. So the way I look at it, definitely an unorthodox way but definitely worked in the end.”

Hahahaha, I’m not crying! I’ve just got Peter and Kelley’s relationship in my eyes. :’)

June 6, 2020

And the gushing continues. Peter talks to Chris Harrison about his relationship with Kelley and it’s a total love fest.

“Post-show, honestly, I’m doing good. I’m extremely happy. It feels so good to be able to say that, and I’m just very hopeful for the future,” he says during an appearance on The Bachelor: The Greatest Seasons. “This is my girl…I am very, very happy with this one.”

And just when we thought that wasn’t already sweet enough, he muses, “We are just really excited for the future. 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…And just enjoy each other. It’s been great….I remember going in, and I wanted that love story more than anything, and I can honestly say it worked out in the end. So, thank you. Thank you, Bachelor Nation for standing by me and all my craziness, but it worked out.”

June 16, 2020

Peter produces a PDA-filled video montage of his and Kelley’s love story that’s so good, even the producers of The Bachelor are put to shame.

Behold:

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July 14, 2020

Yep, remember that thing Peter said about moving to New York City with Kelley? Welp, it looks like they’re actually doing it!

“I’m super excited to take this next step with Kell and move to New York and to see what adventures await,” Peter says in an interview with Entertainment Tonight, while Kelley adds, “We’re not on a reality show anymore, we can take our time. 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.”

July 20, 2020

Barb is back at it. Peter’s mom goes on her own mini press tour, speaking to Life & Style about Peter and Kelley possibly getting engaged. “Now, basically, it’s just enjoying each other’s company and getting to know each other more,” she says. “When the day comes, I’ll let you know!”

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August 19, 2020

Clearly, these two are long past keeping things hidden from the public, because Peter posts a video of the exact first time he and Kelley met in a hotel lobby, which is equal parts cute and 👀.

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December 23, 2020

Peter confirms he and Kelley are moving to NYC. Boring at the time, but important in retrospect considering what happens next:

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Instagram

December 25, 2020

Kelley literally posts a photo of herself wearing socks with Peter’s face on them.

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Which is wild, ’cause….

December 31, 2020

Peter and Kelley call it quits. Peter confirms the news on Instagram, writing a lengthy breakup post:

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A source tells E! News that Peter is the one who ended things, saying, “Peter ultimately was the one who ended it with Kelley, but she 100 percent agreed that they needed time apart. They had been fighting a lot, and the move was very stressful and put a lot of pressure on them.”

January 3, 2021

Kelley fiiiiinally breaks her silence on the breakup days after Peter’s post, saying, “Unfortunately, him and I are in two different stages of our lives and saw our future paths differently.”

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January 4, 2021

A source shuts down rumors that Peter cheated on Kelley, saying, “He would never cheat. 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.”

Meanwhile, another source tells Entertainment Tonight that Peter’s mom Barb was a “major issue” in the relationship and “was very involved and expected to be a major priority within Peter and Kelley’s relationship…she wanted to be Peter’s focus.” Normal!

January 6, 2021

A source tells E! News that Barb put “pressure” on Kelley and Peter—and Kelley thought she was pretty controlling: “Kelley did think Barb was very controlling and overbearing, but she tried to not let it affect their relationship,” says the source. “Barb put a lot of pressure on them, which was definitely hard.”

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Instagram

January 10, 2021

Speaking of moving to NYC, Kelley reveals she’s still heading to New York…where Peter has literally just rented an apartment. Huh! A choice!

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January 12, 2021

Peter opens up to the paps (sure, sure, sure), and muses:

“It hurts. That’s part of it, but I’ll always have an incredible amount of love in my heart for Kelley, so there’s no hard feelings there…It’s obviously a tough time for both of us, but [I] just gotta stay strong and look forward to the future, you know?”

January 25, 2021

Peter and Kelley unfollow each other on Instagram (and he allegedly blocks her!):

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Instagram

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Instagram

February 6, 2021

PLOT TWIST: Peter and Kelley are spotted together in Tampa, the world’s most romantic city, partying indoors ahead of the Super Bowl even though we’re still in the middle of a pandemic.

Meanwhile, E! News drops a report that the couple “knew they were both planning to be in Tampa for the Super Bowl and had plans to meet up. They have been in touch and are working on their relationship.” Oh, and “Peter has been reaching out to Kelley and regrets their breakup. Kelley is very hesitant and thinks he is not ready to commit to her but still has feelings for Peter.”

February 15, 2021

Peter opens up about his relationship on a Zoom call (thx, I hate it), saying, “I’d not seen her since—for a couple of months actually, since things ended. But I did see her and it was a good meeting, for sure. We are on good terms, I will tell you guys that.”

February 17, 2021

Fans decide that Peter and Kelley are fully hanging out together in NYC thanks to some SUSPICIOUS WINDOWS:

peter weber and kelley flanagan's instagram stories of the same windows

Instagram

March 16, 2021

Kelly hops on Kaitlyn Bristowe’s Off the Vine podcast and pretty much shares all the deets on why she and Peter broke up. “On my end, there were just a lot of nonnegotiables in the relationship,” Kelley tells Kaitlyn. “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.”

Kelly also says that she always voiced her concerns about issues that came up while they were dating. “If there is something that I saw as disrespectful in a relationship, I would speak on it and I was pretty vocal…I think communication is huge in a relationship and there were things that essentially I would be like, ‘Hey look, this makes me feel like shit, this makes me feel this way.’ I would always try to talk about my feelings…like, ‘My needs aren’t really being met.’”

Kelley concludes discussing her relationship with Peter and says, “I don’t think I will be in communication with him. It’s a place in my past. I’m focusing on my future wishes. I don’t think it was the healthiest thing for me to keep [my] past and [my] future and I wish him well.”

That brings us up to date, but there’s just one thing left to do….

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You love Bachelor Nation ’ships. So do we. Let’s overanalyze them together. ✔️✔️✔️

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