![Bachelor Peter Weber Holds a Rose in a Blue Suit in Split Image With Kelley Flanagan in Red Dress at After the Finale Rose](https://www.lifeandstylemag.com/wp-content/uploads/2020/04/Peter-Weber-and-Kelley-Flanagan-Relationship-Timeline.jpg?crop=0px%2C16px%2C3264px%2C1849px&resize=940%2C529&quality=86&strip=all)
ABC (2)
Relive Peter Weber and Kelley Flanagan’s Relationship Timeline From ‘The Bachelor’ to Split to Reunion
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!
![Kelley and Peter Dancing on the Bachelor](https://www.lifeandstylemag.com/wp-content/uploads/2020/01/Peter-Kelley-1.jpg?fit=800%2C533&quality=86&strip=all)
ABC/John Fleenor
![Kelley Flanagan Receives a Rose From Peter Weber](https://www.lifeandstylemag.com/wp-content/uploads/2020/04/153384_7411-1.jpg?fit=800%2C1000&quality=86&strip=all)
ABC/John Fleenor
![Kelley Flangan Dressed Like a Pilot During Bachelor Group Date With PEter Weber](https://www.lifeandstylemag.com/wp-content/uploads/2020/04/153428_8985.jpg?fit=800%2C533&quality=86&strip=all)
ABC/John Fleenor
![Peter Weber Holds Hands With Alayah on Bachelor Group Date](https://www.lifeandstylemag.com/wp-content/uploads/2020/04/153526_1020.jpg?fit=800%2C1000&quality=86&strip=all)
ABC/John Fleenor
![Bachelor Peter Weber and Kelley Stand in Bathing Suits During Shaman One on One Date](https://www.lifeandstylemag.com/wp-content/uploads/2020/04/Screen-Shot-2020-04-08-at-10.42.13-AM.png?fit=800%2C423&quality=86&strip=all)
YouTube
![Bachelor Contestant Kelley Flanagan Looks At Peter Weber During one on One Date](https://www.lifeandstylemag.com/wp-content/uploads/2020/04/Screen-Shot-2020-04-08-at-10.44.19-AM.png?fit=800%2C463&quality=86&strip=all)
YouTube
![KELLEY, PETER WEBER The Bachelor Group Date](https://www.lifeandstylemag.com/wp-content/uploads/2020/02/153692_4667.jpg?fit=800%2C640&quality=86&strip=all)
ABC/Francisco Roman
![Peter Weber Smiles in Bachelor Photo Wearing a Black Suit and Holding a Rose in Split Image With Kelley Flanagan Bachelor Contestant Photo in Green Tank Top and Black Jeans](https://www.lifeandstylemag.com/wp-content/uploads/2020/04/Peter-Weber-and-Kelley-Flanagan-Fuel-Romance-Rumors.jpg?fit=800%2C743&quality=86&strip=all)
ABC (2)
![Bachelor Peter Weber and Hannah Ann Sluss Cuddle on a Blanket in Australia During Bachelor Finale](https://www.lifeandstylemag.com/wp-content/uploads/2020/03/154126_9756.jpg?fit=800%2C533&quality=86&strip=all)
ABC/John Fleenor
![Bachelor Contestant Hannah Ann Sluss Wears Red Dress and Stares at Ex Peter Weber in Black Suit During After the Final Rose](https://www.lifeandstylemag.com/wp-content/uploads/2020/03/155318_9118-1.jpg?fit=800%2C640&quality=86&strip=all)
ABC/John Fleenor
![Celebs at Super Bowl LIV Peter Weber](https://www.lifeandstylemag.com/wp-content/uploads/2020/02/celebs-at-super-bowl-liv-peter-weber-feature.jpg?fit=800%2C1000&quality=86&strip=all)
Courtesy of @pilot_pete/Instagram
![MADISON, PETER WEBER](https://www.lifeandstylemag.com/wp-content/uploads/2020/03/154125_2240.jpg?fit=800%2C532&quality=86&strip=all)
ABC Press
![Bachelor Peter Weber Wears Black Suit and Laughs With Madison Prewett in One Sleeved Pink Dress During After the Final Rose](https://www.lifeandstylemag.com/wp-content/uploads/2020/03/155318_9482-1.jpg?fit=800%2C533&quality=86&strip=all)
ABC/John Fleenor
![Madison Prewett Looks Sad After Split Form Peter Weber on The Bachelor](https://www.lifeandstylemag.com/wp-content/uploads/2020/03/Screen-Shot-2020-03-09-at-9.25.36-PM.png?fit=800%2C416&quality=86&strip=all)
ABC
![Is Peter Dating Kelley Flanagan?](https://www.lifeandstylemag.com/wp-content/uploads/2020/03/kelleu.png?fit=800%2C450&quality=86&strip=all)
ABC
![Kelley Flanagan Wears Red Dress at Bachelor After the Final Rose](https://www.lifeandstylemag.com/wp-content/uploads/2020/04/155318_2500-2.jpg?fit=800%2C1202&quality=86&strip=all)
ABC/John Fleenor
![Kelley and Peter Weber Three on One Date Bachelor](https://www.lifeandstylemag.com/wp-content/uploads/2020/02/Screen-Shot-2020-02-10-at-9.39.48-PM.png?fit=800%2C441&quality=86&strip=all)
ABC
![Kelley With Peter Weber from the Bachelor](https://www.lifeandstylemag.com/wp-content/uploads/2020/01/Peter-Kelley.jpg?fit=800%2C533&quality=86&strip=all)
ABC/John Fleenor
![Bachelor Peter Weber Holds Girlfriend Kelley Flanagan Wearing Camo in the Woods](https://www.lifeandstylemag.com/wp-content/uploads/2020/05/kelleyflanagan_97157745_158676142293633_1842209344632320319_n.jpg?fit=800%2C800&quality=86&strip=all)
Courtesy Kelley Flanagan/Instagram
![Bachelor Peter Weber and Kelley Flanagan Sit on Boat Together](https://www.lifeandstylemag.com/wp-content/uploads/2020/04/pilot_pete_100969862_939981216453954_359721205417648135_n.jpg?fit=800%2C999&quality=86&strip=all)
Courtesy Peter Weber/Instagram
![Bachelor Peter Weber Goofs Around With Girlfriend Kelley Flanagan](https://www.lifeandstylemag.com/wp-content/uploads/2020/06/pilot_pete_102554885_748477369230664_8812752675820566572_n.jpg?fit=800%2C1000&quality=86&strip=all)
Courtesy Peter Weber/Instagram
![Peter Weber and Kelley Flanagan Relationship Timeline](https://www.lifeandstylemag.com/wp-content/uploads/2020/07/sweetnums_119419065_117982779864598_6663764214954406283_n.jpg?fit=800%2C1000&quality=86&strip=all)
Courtesy Barbara Weber/Instagram
![Kelley Flanagan Says Reason Bachelor Peter Weber Didn't Pick Her](https://www.lifeandstylemag.com/wp-content/uploads/2020/09/kelleyflanagan_118355906_227442322010446_6716078521667017656_n.jpg?fit=800%2C800&quality=86&strip=all)
Courtesy Kelley Flanagan/Instagram
![Peter Weber and Kelley Flanagan Have Come So Far Since 'The Bachelor' — See Their Relationship Timeline](https://www.lifeandstylemag.com/wp-content/uploads/2020/09/Peter-Weber-Kelley-Flanagan-Relationship-Timeline-December-2020.png?fit=732%2C1312&quality=86&strip=all)
Courtesy of Peter Weber/Instagram
![peter-kelley-bachelor-split](https://www.lifeandstylemag.com/wp-content/uploads/2020/12/peter-kelley-bachelor-split-1.jpg?fit=800%2C833&quality=86&strip=all)
Kelley Flanagan/Instagram
![Peter Webers Mom Barbara Reveals He and GF Kelley Are in No Rush to Get Engaged](https://www.lifeandstylemag.com/wp-content/uploads/2020/07/Peter-Webers-Mom-Barbara-Reveals-He-and-GF-Kelley-Are-in-No-Rush-to-Get-Engaged.jpg?fit=800%2C800&quality=86&strip=all)
Chris Pizzello/Invision/AP/Shutterstock; Courtesy of Barbara Weber; John Fleenor/ABC
![Peter Weber and Kelley Flanagan Move to New York City](https://www.lifeandstylemag.com/wp-content/uploads/2021/01/119215326_190362039352915_1338210595517603313_n.jpg?fit=800%2C1000&quality=86&strip=all)
Courtesy Peter Weber/Instagram
![Bachelor Contestant Kelley Flanagan Headshot in Green Turtleneck and Black Jeans](https://www.lifeandstylemag.com/wp-content/uploads/2020/04/153300_1294-5.jpg?fit=800%2C1200&quality=86&strip=all)
ABC/Maarten de Boer
![Are Peter Weber and Kelley Flanagan Back Together](https://www.lifeandstylemag.com/wp-content/uploads/2021/01/118472018_178422443888276_7328278990008580670_n.jpg?fit=800%2C1000&quality=86&strip=all)
Courtesy Peter Weber/Instagram
![Peter Weber and Kelley Flanagan Thanksgiving](https://www.lifeandstylemag.com/wp-content/uploads/2020/11/Screen-Shot-2020-11-27-at-8.51.43-AM.png?fit=756%2C1352&quality=86&strip=all)
Courtesy Peter Weber/Instagram
![kelley-flanagan-peter-weber-at-good-bar-nyc-together-feb-2021](https://www.lifeandstylemag.com/wp-content/uploads/2021/02/kelley-flanagan-peter-weber-at-good-bar-nyc-together-feb-2021.jpg?fit=800%2C800&quality=86&strip=all)
![Peter Weber and Kelley Flanagan Back Together](https://www.lifeandstylemag.com/wp-content/uploads/2022/09/Peter-Weber-Kelley-Flanagan-Back-Together-0001.png?fit=800%2C800&quality=86&strip=all)
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