Here’s a Definitive Timeline of Peter Weber and Kelley Flanagan’s Relationship Before They Broke Up

Mehera Bonner
·9-min read
Photo credit: Instagram
Photo credit: Instagram

From Cosmopolitan

Remember back in February 2020 when Peter Weber’s season of The Bachelor aired? I believe it was approximately 10 years ago? Yeah, well, he’s still out here having the ~most dramatic season ever~, and the damn show isn’t even on anymore. As a reminder, Peter got engaged to Hannah Ann Sluss:

Photo credit: Giphy
Photo credit: Giphy

Then he dramatically broke up with her:

Photo credit: Giphy
Photo credit: Giphy

And then he got back together with Madison Prewett:

Photo credit: Giphy
Photo credit: Giphy

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

Photo credit: Giphy
Photo credit: Giphy

You’d think Peter would want to take a break from romance after ending two relationships back-to-back, but apparently not, because now he’s out here dating Kelley Flanagan, y’all. It all started during 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!

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

Photo credit: Instagram
Photo credit: 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.

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.

Photo credit: Instagram
Photo credit: 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 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’s been posting TikToks from Kelley’s house based on the freakin’ rug he’s standing on:

Photo credit: Instagram
Photo credit: Instagram

He goes ahead and tags her in this Insta video:

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:

April 7, 2020

Peter gives an update on his relationship status with Kelley—FINALLY. During his time on Nick Viall’s Viall Files podcast, he says:

“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 puts us all out of our misery by making their relationship Instagram official. It’s so cute, it frickin’ hurts, man.

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. He says:

“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 cute enough, Peter adds, “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.


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. They’re being super careful not to jump the gun and think about larger commitments like marriage and children though.

“We’re not on a reality show anymore, we can take our time,” Kelley adds. “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 went on her own mini press tour, speaking to Life & Style about Peter and Kelley possibly getting engaged (!), saying Peter and Kelley are taking each day as it comes. “Now, basically, it’s just enjoying each other’s company and getting to know each other more,” she said. “When the day comes, I’ll let you know!” She then added that Peter and Kelley are “madly in love” and “very compatible.”

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 👀.

December 31, 2020

Bad news, Peter/Kelley fans: The Bachelor couple has called it quits. :( Peter was the bearer of bad news on Instagram, writing a lengthy breakup post.

"Love is a funny thing. It can make you 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. These moments in life always hurt, but in my opinion that shows you it was worth the time you spent together. Thank you Kelley."

Sad to see them join the many other couples who broke up during the dumpster fire that is 2020. Ho hum.

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