Viewers saw the beginning of Peter Weber and Kelley Flanagan’s love story unfold during his season of The Bachelor. Kelley made it all the way to the final five before Peter realized he had stronger relationships with the other women. Peter sent her home, but Kelley didn’t leave without reminding Peter he made a huge mistake. At the end of his season, Peter ended up proposing to Hannah Ann, but the relationship only lasted a couple of months.
Shortly after Peter’s failed engagement, he tried to re-develop his relationship with Madison. However, the disapproval from his mom, and Madison’s uncertainty about the relationship at the After The Final Rose special, led them to split a few days later. Shortly after the airing of the finale, rumors began to circulate that Peter and Kelley had reconciled. After the rumors started, pictures of the couple in Chicago were all over the internet. This was the beginning of the short-lived, drama-filled relationship.
Met Before The Bachelor
Peter and Kelley met in August 2019, less than a month before Peter began filming for the dating reality series. The former couple met in a hotel lobby where they both staying for separate weddings. Even though Kelley told Peter she was a possible contestant for The Bachelor, he had no idea he would see her again.
She Competed On His Season
When Kelley exited the limo on night one, Peter recognized her right away. The pair had a whirlwind romance on the show, but it did not last in the end. She later alleged that ABC producers tried to keep her from Peter. "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, " she revealed to Us Weekly in April 2020.
They Dated After His Season Ended
In February 2020, shortly after Peter called off his engagement, he saw Kelley at a Super Bowl party in Miami. A month later, the couple was spotted hanging out together in her home city of Chicago. Peter and Kelley seemed to be happy together and in a pleasant mood.
First Break Up
The pilot announced his split from the lawyer in a lengthy Instagram post he shared on New Year's Eve. "While our relationship was filled with countless beautiful memories, our relationship simply didn’t work out in the end," Peter wrote in his statement. "Kelley is someone I will always have a special love for." Kelley was caught off guard as she made her own Instagram post stating she wanted to process the break-up before making a statement.
Reconciliation
In February of this year, Peter and Kelley were spotted at a nightclub in Florida for the Super Bowl weekend. The pair reconciled for a short time, even spending Valentine's Day together. During an interview on the Chicks In The Office podcast, Kelley confirmed the reconciliation, claiming they had a fantastic date together.
Final Spilt
During the Chicks In The Office interview, Kelley also confirmed the two are no longer together. They officially called it quits shortly after they went on the Valentine's Day date. She found out some undisclosed news about Peter and essentially told him to "Get the hell out of [her] life."
Even though Peter and Kelley's relationship didn't work out, it was the most successful one Peter had been in from the franchise. He was sent home after the overnight date during Hannah Brown's season of The Bachelorette, he broke off his relationship with Hannah Ann, and a relationship didn't pan out for him and Madison after they broke up a couple days after the After the Final Rose special. It seems as though Peter may be unlucky in love.
Sources: Us Weekly, Chicks In The Office