Ups and downs. Former Bachelor star Peter Weber and former contestant Kelley Flanagan rekindling their relationship after season 24 came as a shock to many fans, but they proved second chances are worth a try. Unfortunately, the pair called it quits in December 2020 after nearly nine months together but sparked reconciliation rumors less than a month later.
The Bachelor Nation duo first met prior to her appearance as a contestant on Peter’s season, and they reconnected months after filming. “My relationship with Kelley has been … serendipitous,” Peter gushed during an April 2020 episode of Nick Viall’s “The Viall Files” podcast before they officially announced they were dating again. “You go all the way back to the very beginning — us running into each other before any of this stuff started. Obviously, the show happened and it didn’t work out for us.”
Kelley made it to the top five of Peter’s season but was eliminated during a group date before hometowns. He went on to get engaged to Hannah Ann Sluss during the finale in Australia but broke things off two months later because he still had feelings for runner-up Madison Prewett. He and Madi fizzled out after briefly reconnecting during After the Final Rose in March 2020.
Peter then surprised all of Bachelor Nation later that month when he started quarantining with Kelley in her hometown of Chicago amid the coronavirus pandemic. They followed their hearts one month later and went Instagram official as a couple.
They were completely smitten with each other until their shocking split. Peter’s mom, Barbara Weber, exclusively told Life & Style the reality couple’s romance was “gradual” this time around, and they had “real time” to get to know each other.
“It’s nice because she reminds me very much [of] Peter,” the reality mom explained about the lawyer. “They’re so compatible. Peter got to meet [Kelley’s] mom — the whole family — and it’s great because I come from Cuba and her mom comes from Greece, and we are so much alike! We’ve raised our kids the same way, very warm and the closeness of family is really important to us. Her family and mine are just basically the same in that respect.”
Scroll through the gallery below to see Peter Weber and Kelley Flanagan’s full relationship timeline!