Peter Weber, affectionately known as “Pilot Pete,” captivated audiences during his tumultuous season of The Bachelor. His journey for love was anything but smooth, marked by broken engagements and rollercoaster romances. For fans who followed his journey, a burning question often arises: Who Did Peter Weber Marry? While his season didn’t end in a traditional marriage, his post-show dating life, particularly his on-again, off-again relationship with Kelley Flanagan, has kept him in the spotlight. This article delves into the complete timeline of Peter Weber and Kelley Flanagan’s relationship, along with a look at his Bachelor season, to answer the question of who, if anyone, Pilot Pete ultimately married.
August 2019: A Serendipitous Encounter Before The Bachelor
Before the cameras even started rolling for Peter Weber’s season of The Bachelor, fate intervened. Kelley Flanagan and Peter had a chance encounter at a hotel. Flanagan was attending a friend’s wedding at the same hotel where Peter was present for his 10-year high school reunion. This initial meeting occurred as Flanagan was contemplating whether to join the reality dating show. She viewed the encounter as a sign, a serendipitous moment that encouraged her to take the plunge and compete for Peter’s heart on The Bachelor.
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Image of Kelley Flanagan and Peter Weber from their initial meeting before The Bachelor, highlighting their early connection.
Fall 2019: Kelley Competes for Peter’s Affections on The Bachelor
A month after their initial meeting, Kelley officially became a contestant on Peter Weber’s season of The Bachelor. However, her experience within the Bachelor mansion wasn’t as smooth as their first encounter. Kelley later revealed in an interview that she felt producers interfered with her connection with Peter. She expressed that off-camera, Peter seemed genuinely interested, but during filming, especially on their one-on-one date, his demeanor changed, becoming distant and seemingly influenced by producers. Kelley believed that producers were preventing them from developing a genuine relationship, manipulating the narrative behind the scenes. Despite her efforts to connect with Peter and express her concerns about production interference, Kelley was eliminated before the hometown visits, much to the surprise of some viewers who saw their initial spark.
March 10, 2020: Kelley Attends After the Final Rose
Intriguingly, Kelley Flanagan was present in the audience for the After the Final Rose finale episode of Peter Weber’s Bachelor season. Her appearance was notable because she was absent from the Women Tell All special, raising eyebrows and fueling speculation about her relationship with Peter post-elimination. During the After the Final Rose episode, Kelley witnessed the dramatic conclusion of Peter’s season, including his breakup with Hannah Ann Sluss, his attempt to reconcile with Madison Prewett, and the infamous confrontation with his mother, Barb. Throughout this televised drama, Kelley remained silent, further adding to the mystery surrounding her presence.
March 11, 2020: Peter’s Mother, Barb, Shows Support for Kelley
Adding another layer to the unfolding drama, Peter Weber’s mother, Barb, publicly expressed her admiration for Kelley Flanagan. In a comment on Kelley’s Instagram, Barb described her as “The Most Beautiful, Elegant, Classy, Intelligent Stylish Girl in the world!!!!” This public endorsement from Barb was particularly noteworthy considering that at the time, Peter was still attempting to pursue a relationship with Madison Prewett, the runner-up from his season. Barb’s comment seemed to signal a clear preference for Kelley over Peter’s other connections from the show.
March 12, 2020: Kelley Denies Romance Rumors
Despite the growing speculation and Barb’s public approval, Kelley Flanagan initially denied any romantic involvement with Peter Weber after The Bachelor. She addressed rumors circulating online, including claims that she was pregnant and in a relationship with Peter. In an interview with E! News, Kelley firmly stated, “I have heard that. I heard that I’m pregnant and I also heard that I’m with Peter right now. I’m not with Peter. I promise I’m not dating Peter. I’m not dating Peter.” At this point, Kelley maintained that she and Peter were not together, despite mounting evidence and fan theories suggesting otherwise.
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Image of Kelley Flanagan and Peter Weber, capturing the period when they publicly denied relationship rumors despite spending time together.
March 23, 2020: Chicago Riverwalk Outing
Just days after denying romance rumors, Kelley and Peter were spotted together in Chicago, Kelley’s hometown. They were seen enjoying time on the Chicago Riverwalk with Dustin Kendrick, another contestant from Hannah Brown’s season of The Bachelorette. This public outing occurred while Illinois was under a stay-at-home order due to the pandemic, making their public appearance even more noticeable. The sighting further fueled speculation that Kelley and Peter were more than just friends, despite their public denials.
April 12, 2020: TikTok Quarantine and Growing Closeness
As quarantine measures intensified in April 2020, Peter Weber began creating TikTok videos, a trend many embraced during that time. It quickly became apparent that he was quarantining with Kelley Flanagan. She started appearing in his TikToks, along with Dustin Kendrick. The trio participated in viral challenges like the “Flip the Switch” challenge and created lip-sync videos. Kelley even made a cameo in one of Peter’s Cameo videos. Their consistent presence together in social media content made it increasingly clear that their relationship was evolving beyond friendship.
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Image of Peter Weber and Kelley Flanagan in a TikTok video, representing their quarantine period and growing relationship.
Peter addressed the nature of their relationship in an interview with Nick Viall. He explained that he had traveled to Chicago to support Kelley during a family matter and decided to stay with her as quarantine measures began. While acknowledging their close bond and “good chemistry,” Peter maintained that they were not officially dating at the time. He stated he was taking things “really, really slow” after his recent engagement and subsequent breakup from The Bachelor. However, he admitted to Kaitlyn Bristowe on her podcast that he had a “crush on Kelley,” indicating his growing romantic feelings.
April 28, 2020: Officially a Couple
By late April 2020, the relationship between Kelley Flanagan and Peter Weber transitioned from quarantine companionship to official couple status. Sources confirmed to PEOPLE that they were indeed dating and “a couple.” The pair seemed to subtly confirm the news themselves through a TikTok video where they lip-synced to Akon’s song “Don’t Matter,” further solidifying their relationship in the public eye.
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Image of Peter Weber and Kelley Flanagan, marking their official confirmation as a couple after weeks of speculation.
May 2, 2020: Family Approval and Instagram Official
The Weber family wholeheartedly embraced Kelley into their fold. Peter made their relationship Instagram official with a photo of him kissing Kelley in a plane cockpit, captioned “You caught me. Let the adventures begin.” His mother, Barb, enthusiastically celebrated the relationship with a photo collage and the caption “Serendipity,” clearly indicating her strong approval, especially in contrast to her reservations about Madison Prewett. Peter’s father also shared photos of the couple, captioning them “Happiness is finding your copilot,” further cementing the family’s support for Kelley and Peter’s relationship.
May 12, 2020: Tandem Bike Rides and California Social Distancing
As they settled into their relationship, Kelley and Peter relocated to California, where Weber’s family resided, to continue social distancing together. They were photographed enjoying a tandem bicycle ride, showcasing their playful and adventurous side as a couple. Kelley also posted a photo of Peter on her Instagram, playfully captioning it, “I know I’m a handful.. good thing you have two hands 😜😘,” solidifying their image as a happy and affectionate couple.
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Image of Peter Weber and Kelley Flanagan riding a tandem bicycle, illustrating their public displays of affection and shared activities.
May 25 – August 18, 2020: “Ray of Sunshine,” Birthday Celebrations, and Anniversary
Throughout the summer of 2020, Peter and Kelley continued to share glimpses of their relationship on social media. Peter referred to Kelley as his “little ray of sunshine” in an Instagram post. They celebrated Peter’s 29th birthday with family and friends, with Kelley posting a loving tribute to him on Instagram. In August, Peter commemorated the one-year anniversary of their first meeting at the hotel, expressing his appreciation for Kelley and their unexpected journey together. These public declarations highlighted the seemingly strong and happy phase of their relationship.
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Image of Peter Weber and Kelley Flanagan celebrating Peter’s birthday, depicting a joyful moment in their relationship timeline.
December 31, 2020: First Breakup
The seemingly stable relationship took a turn as Peter Weber announced on New Year’s Eve 2020 that he and Kelley Flanagan had decided to break up. In an Instagram post, Peter described love as “a funny thing” and shared that while they had “countless beautiful memories,” their relationship “simply didn’t work out in the end.” This breakup came as a surprise to many fans, especially after their earlier plans to move to New York City together did not materialize. Shortly after the announcement, Peter moved to New York City alone.
March 2021: Brief Reunion and Final Split
Despite their New Year’s Eve breakup, Kelley revealed in a March 2021 podcast interview that she and Peter had briefly rekindled their romance shortly after their initial split. However, this reunion was short-lived, and they broke up again in February 2021, after Valentine’s Day. Kelley cited “non-negotiables” in the relationship as the reason for the final split, suggesting unresolved issues and differing expectations. She also revealed that their final breakup was “ugly,” and she ultimately told Peter to “get the hell out of my life,” indicating a contentious end to their romantic relationship. Peter later stated on his podcast that he had “100 percent moved on” and that they were not “right for each other.”
September 2022 – April 2023: Rekindled Romance and Final Breakup (Again)
In a surprising turn of events, Peter and Kelley sparked reconciliation rumors in September 2022 when they were seen dancing together at a gala in Florida. They officially confirmed they were back together in October 2022, marking their third attempt at a relationship. They shared photos on Instagram from Yankee Stadium and the Empire State Building, seemingly happy to be together again. They enjoyed a romantic cruise and attended a movie premiere together in early 2023. However, this reconciliation was also not to last. In April 2023, Peter confirmed their final breakup while attending a beauty convention, answering a question about his “future wife” by stating, “I still gotta find her.”
June 2023: Kelley Moves On
Months after her final split from Peter, Kelley Flanagan debuted her new boyfriend, Ari Raptis, on Instagram in June 2023. Sources indicated they had initially met the previous summer and recently rekindled their connection. This marked a clear end to the Peter and Kelley saga, with both moving on to new chapters in their lives.
Conclusion: Peter Weber’s Marital Status
So, who did Peter Weber marry? As of the latest updates, Peter Weber has not married anyone from The Bachelor or Kelley Flanagan. His journey on The Bachelor ended with a broken engagement, and his subsequent relationship with Kelley Flanagan, despite its passionate and cyclical nature, ultimately did not lead to marriage. Peter Weber remains unmarried, continuing his search for his “future wife.” His relationship timeline with Kelley Flanagan, filled with dramatic ups and downs, serves as a compelling example of the complexities of relationships, especially those that begin in the unique environment of reality television.
