Kelley Flanagan quickly became known as "the normal one" on this season of The Bachelor, and TBH, it totally makes sense — she didn’t stir the pot just for funsies, lose it over a bottle of champagne, or exhibit a range of bizarre tongue expressions (looking at you, Mykenna). She also carried herself with a maturity and grace that made many fans hope she’d end up with the final rose. So, now that you’re aware Peter Weber ultimately chose Madison Prewett, you’re probably dying to know: Is Kelley Flanagan single after The Bachelor? Rumors are flying, but don’t fret — I plan to address them all.
First, let’s review the facts. Based on Flanagan’s Instagram posts as of late, several things are clear: She’s still based in Chicago, she’s back to practicing property law at her family’s law firm Flanagan Bilton, and she’s been traveling a ton (jetting off to Aspen, Italy, Miami Beach in just the last few months). Meanwhile, her ex’s mom has been sliding into her IG comments (more on that later).
And then, things get juicy. According to Reality Steve, there’s a rumor that Flanagan and Weber reconnected for an intimate weekend in Miami during the weekend of the Super Bowl — after he broke off his engagement with Hannah Ann Sluss, but before his reunion with Madison Prewett. (Elite Daily has reached out to reps for both Flanagan and Weber for comment and did not hear back in time for publication.)
In a March 11 blog post in which Reality Steve commented on Flanagan’s appearance on ATFR, he wrote:
Reality Steve also added that "someone close to the situation" gave him reason to believe the rumors. In commenting on the finale, he wrote:
Assuming he’s referring to Flanagan in saying there were “other girls” in the picture, now would be the time to note that there’s other evidence that supports this possibility.
Exhibit A: Weber reportedly went to a Valentine’s Day party at Stassie Karanikolaou’s digs, and Kylie Jenner — who was also attended — posted a video from the festivities. In the background of the video, you can hear Weber say Flanagan’s name. There’s no way of knowing exactly what he was saying about her, but the fact that she was on his mind during V-Day is pretty telling.
Exhibit B: One Redditor claims that their coworker was sitting behind Weber’s family during ATFR, and picked up some seriously game-changing deets:
Obviously, there’s no way to confirm whether or not their story is legit. Still, if you were wondering WTF Barb was muttering all that time to Peter Sr. and straining to read her lips, that’s quite a juicy tidbit.
Unfortunately, these are all still rumors and speculations at this point. One thing’s for sure, though: Flanagan would def have Barb’s seal of approval.
On March 11, Flanagan shared a pic from the live viewing of the finale with the caption “That’s a wrap! What a great experience and will always be grateful for the opportunity to join season 24!” Barb commented, “We need to do lunch and shopping for the day,” leaving many fans scratching their heads about their relationship. Barb also gushed about Flanagan in one of her other Instagram comments, writing: “The Most Beautiful, Elegant, Classy, Intelligent Stylish Girl in the world!!! You were and will always be my Fav rav." I don’t know about you, but I’m officially baffled. Wasn’t Sluss the favorite — the one inspired the legendary "bring her home" speech? It’s worth mentioning that Barb doesn’t follow Madison Prewett (no shocker there), nor does she follow Sluss. Flanagan, however, follows the entire Weber family.
In a March 12 interview with Us Weekly, Flanagan revealed that she felt like Barb was "rooting for her," and that Weber’s mom even had producers find her so they could meet at the finale show. "She just started hugging me profusely," Flanagan told Us Weekly. “She was like, ‘You were my favorite since day one! I love you! You’re beautiful!’"
BTW — Like Flanagan, Barb has deep Chicago roots. Not only was she the queen of Chicago’s Lakefront Festival and a cheerleader for the Chicago Honey Bears, but she also won the title of Miss Illinois.
It goes without saying that Flanagan instantly had a special connection with Peter from the start of the season — in part because she had already met him while attending a wedding in Malibu. Weber, who was attending his 10-year high school reunion, happened to be staying at the very same hotel. That very encounter is what inspired her to go on the show, and some of the other ladies believed it gave her an advantage. Weber sent Flanagan home after a three-on-one date with Sluss and Victoria Fuller, but since then, he’s had nothing but nice things to say about her.
Many fans have long been convinced that even though Flanagan finished in fifth place, that she ultimately won Peter’s heart. This is partly because she made a super sus appearance at the finale filming, at which she was sitting next to none other than engagement ring designer of your dreams, Neil Lane. Chris Harrison even noted that it was “important” that she was there. (Why must you mess with my mind, Chris Harrison?) As it turns out, her appearance on the “After The Final Rose” episode may just have been a clever diversion. Or was it?
In a Feb. 10 interview with Entertainment Tonight, Weber called himself Flanagan’s “biggest fan.”
“Kelley is one of the smartest people I’ve met,” he told the publication. “[She has] such a strong presence … I definitely had questions at first if she was really ready and wanted this. I was wrong, she truly was.”
So, was a spark rekindled between Weber and Flanagan? Or is she moving forward, and gearing up to crush it on Bachelor in Paradise? This case isn’t quite closed, fam, and something tells me only a certain Chicago lawyer can close it.
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