Kelley Flanagan & Peter Weber Are Instagram Official! A Look Back at How Their Relationship Evolved
She may not have gotten the final rose, but Kelley Flanagan managed to snag Peter Weber's heart
The course of Bachelor love never did run smooth. Shakespeare wrote that, right? Or maybe it was Chris Harrison.
Either way, Peter Weber's 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 that after the cameras stopped rolling, there would be even more to unpack?
The 28-year-old pilot is now dating Kelley Flanagan, also 28, who was eliminated before hometowns. It hasn't necessarily been a smooth ride for the couple: There was some turbulence in the form of broken engagements and broken hearts, but somehow they've made a safe landing in the middle of a worldwide pandemic and have become Instagram official!
Here's a look back at their relationship history:
August 2019, A Chance Encounter
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: Competing for 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 Attends After the Final Rose
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: Barb Weighs In
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 Shuts It Down
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 and Peter 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: TikToking Together
Around this time, the former Bachelor started to make TikTok videos (aren'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 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.”
“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.”
“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: They're Officially a Couple
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.
May 2, 2020: The Whole Fam Is Making It 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: On a Bicycle Built for Two
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!
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.