Here’s a timeline of Peter Weber and Kelley Flanagan’s relationship

NEW YORK, NEW YORK - JANUARY 10: Kelley Flanagan and Peter Weber attend the "Plane" New York Screening at AMC Lincoln Square Theater on January 10, 2023 in New York City. (Photo by Jamie McCarthy/Getty Images)
NEW YORK, NEW YORK - JANUARY 10: Kelley Flanagan and Peter Weber attend the "Plane" New York Screening at AMC Lincoln Square Theater on January 10, 2023 in New York City. (Photo by Jamie McCarthy/Getty Images) /

Another popular Bachelor Nation couple has called it quits (again). After a reconciliation, it appears that Season 24 Bachelor Peter Weber and contestant Kelley Flanagan have ended their relationship again.

Though neither Peter nor Kelley has addressed the possible breakup via social media, Peter alluded to being single on an Instagram appearance on the account @beautybybcanada. After some witty banter about making sure he is properly groomed for his future wife, the esthetician quips that Peter is “still single” and in Calgary, to which Peter replies, “I am” (via E! News).

Though Peter could have confirmed he was visiting Canada then, he also brings up still needing to find his future wife. This doesn’t sound like something a man in a relationship would say. However, Peter and Kelley’s relationship has been anything but conventional.

A look back at the timeline of Peter Weber and Kelley Flanagan’s tumultuous relationship

August 2019:

We learned from watching Peter’s season that his and Kelley’s connection was unique, as they had met before filming began. In August of 2019, about a month before filming for The Bachelor began, they met in a hotel lobby, where they were both staying as guests of two separate weddings.

September 2019:

The Bachelor begins filming.

January 2020:

Peter Weber’s season of The Bachelor airs, and it is clear from the beginning that Kelley and Peter have great chemistry. Both passionate about their careers and confident, they made a great couple.

February 11, 2020:

The episode airs when Peter sends Kelley home. Kelley did not quite make it to hometown dates, which shocked viewers of the show. On an awkward three-on-one date (do we all agree that those are the absolute worst?), we saw Hannah Ann and Victoria F. receive roses, and Kelley sent home packing. Fans likely remember the outrage most felt over this, as Kelley had been one of the most mature girls in the house. On a side note, in their time together since the show wrapped up, it is worth wondering how many times Kelley has given Peter a hard time for sending her home so early.

March 2, 2020:

Peter’s “Women Tell All” episode airs. That was certainly one to remember, with all of the drama in the house throughout the season. One memorable thing about the episode was that Kelley was absent. According to Reality Steve, Kelley had not been invited.

March 9, 2020:

The finale of The Bachelor airs, followed by After the Final Rose. We learn that Peter proposes to Hannah Ann Sluss, much to his mother’s delight (the famous Barb!!). However, when we catch up with Peter, we learn the engagement has already been broken off, and he wants to make things work with Madison Prewett. Is anyone else still furious with Peter for taking Hannah Ann’s first engagement from her when he knew he was not serious about her, or is it just me?

March 12, 2020:

Peter Weber announces via Instagram that he and Madison Prewett have decided not to pursue their relationship further.

May 2, 2020:

Peter shares a photo of himself kissing Kelley on his Instagram in an airplane, with the caption, “You caught me. Let the adventure begin.”

December 31, 2020:

In a now-deleted Instagram post, Peter announces that he and Kelley have gone their separate ways. Peter wrote: “Love is a funny thing. It can make you feel on top of the world and 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.” Peter then thanked Kelley for their time together. Kelley would confirm the news on her Instagram account a few days later.

February 7, 2021:

Peter Weber and Kelley are spotted together at parties during the Super Bowl weekend and at the event itself, and sources claimed that Peter and Kelley were attempting to work on their relationship. An insider claimed: “Kelley is very hesitant and thinks he’s not ready to commit to her, but still has feelings for Peter” (via Yahoo!).

May 20, 2021:

Kelley Flanagan appears on the Chicks in the Office podcast and spills some major tea about her relationship and breakup with Peter Weber. Aside from explaining that it felt that she and Weber were too different of people, she also claimed the relationship ended very badly, and she told him to lose her number. Despite her requests to announce the breakup on January 3, which producers of The Bachelor also asked for, Weber announced the breakup on New Year’s Eve, much to her frustration.

May 25, 2021:

Peter shares his side of the story on his podcast with Dustin Kendrick (also from Hannah Brown’s season), called Bachelors in the City. Weber called Flanagan calculating, accusing her of attempting to headline grab when they had already broken up nearly six months. Needless to say, it did not seem a reunion would be in the works for this couple.

August 10, 2022:

Reconciliation rumors spark when Peter Weber and Kelley Flanagan are spotted together at a Chicago Cubs game and photographed together at an airport.

October 14, 2022:

Peter Weber confirms his reunion with Kelley on his Instagram page, with a cute photo of him and Kelley at a baseball game with the caption “Home Run.” Interestingly enough, that post has been deleted.

May 1, 2023:

The post by @beautybybcanada is posted, seemingly confirming the breakup.

Of course, nothing should be believed until it comes straight from the source. However, considering it seems that the couple has purged most of their content together since their reunion, it seems likely that Peter Weber and Kelley Flanagan have split up again. At this point, it seems unlikely that either will go to social media to confirm the breakup.

If the pair split up again, perhaps we could see Kelley appear on the beach for Bachelor in Paradise this summer. In the past, she expressed being open to it.

Next. The Bachelor and Bachelor in Paradise have been renewed at ABC. dark

Only time will tell!

Overall, it seems once again that Peter Weber’s season was a letdown, as he is once again single.