Peter Weber Dating History: From Madison Prewett to Brook Sill

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Former Bachelor contestant Peter Weber might have finally met The One.

In June 2025, the reality TV personality posted a heartwarming picture of himself and Brook Sill on Instagram, confirming they were in a relationship. Earlier that month, Weber had hinted at being in a special relationship during an episode of “The Ben & Ashley I. Almost Famous” podcast on iHeartRadio.

Ever since Weber graced our screens during the 15th season of ‘The Bachelorette’, there has been much curiosity about his love life. Later, he was chosen as the Bachelor for season 24 and proposed to Hannah Ann Sluss. However, their relationship didn’t last, and he later moved on with Madison Prewett. But that relationship also didn’t work out for long.

Ever since fans have wondered about who Weber has been (or hasn’t been) dating, let us delve into his romantic past as we continue scrolling: a glimpse of his dating history unfolds.

Calee Lutes

Lutes and Weber had a “deeply committed” long-distance romance that began when they matched on a dating app in 2018. However, their relationship took an unexpected turn as Weber decided to end things before the festive season in late 2018.

In an interview with Entertainment Tonight in July 2019, Lutes shared that their relationship ended just two days before Christmas. He suggested the breakup because it was about to get more serious, but he didn’t provide a specific reason. Lutes was left heartbroken and taken aback by this unexpected turn of events. She speculated that he might have found someone else, only to discover, upon checking his Instagram followers, that he had been working with a producer for The Bachelorette instead.

Back in March 2019, when I spotted her name among the contestants for that show, everything fell into place like a perfectly crafted symphony. And you know what? Guess who swiftly wiped clean any trace of that talented musician, Lutes, from his social media? Yours truly!

According to Lutes, it was in October that he confessed his love for the first time, a fact he shared with ET. He expressed his desire for me to relocate to Los Angeles to live with him, and his intention was for us to share an apartment.

Hannah Brown

In the 15th season of ‘The Bachelorette’, Brown and Weber crossed paths, but in the end, it was Brown who ended their relationship. However, reports suggest they reconnected in February 2020 and engaged in an intimate encounter. Coincidentally, this period also overlapped with when Weber was shooting his own season of ‘The Bachelor’.

Brown detailed the alleged situation in her memoir, God Bless This Mess.

Speaking candidly about my experiences, I believe that sharing that particular tale offers an authentic and exposed glimpse into my life at the time. As exclusively shared with Us Weekly, including the February 2020 encounter in the book was essential because it marked the beginning of a tumultuous period that included my brother’s overdose, the quarantine crew drama, and ultimately led me to seek help when I needed it most. In hindsight, those events formed a perfect storm of poor decisions, but they served as a turning point in my life. I believe this story resonates with many, even if not everyone can relate to the specific circumstances, it certainly echoes the struggle of making regrettable choices during difficult times – something that I think many young women can identify with.

From the time they initially crossed paths on ‘The Bachelorette’ in 2019, through to April 2020 when Hannah Brown announced her single status, their romantic journey together unfolded and eventually came to an end.

Madison Prewett

As a diehard fan, I can’t help but share my excitement about the magical encounter between Prewett and Weber during the 24th season of “The Bachelor.” From the very beginning, luck seemed to be on her side as she was the one who received the coveted first one-on-one date. But that wasn’t all! Their connection was so strong that they quickly moved on to meet each other’s families shortly after their initial introduction. It was a whirlwind of romance that had me glued to my TV screen!

Barbara Weber expressed, “Indeed, it appears he’s quite impressed by you, and I must say, that brings me great joy as I genuinely admire you too,” she shared with Madison following their encounter.

During filming, Prewett confided in Peter that she was unsure whether they could maintain a relationship if he became intimate with other women within the show’s fantasy suites. True to her word, when Weber acknowledged he had been intimate with others, Prewett ended their date and left.

Eventually, Prewett expressed to Peter that she felt their beliefs weren’t compatible and chose to exit the program. Later, he proposed to Hannah Ann Sluss. When they ran into each other at the reunion show, they gave dating another try – however, this brief relationship didn’t last long, ending on March 12, 2020, just two days after their reunion.

Hannah Ann Sluss

During the final episode of the 24th season of “The Bachelor,” which was filmed in November 2019, Sluss and Peter announced their engagement. However, their relationship didn’t last long as Peter confessed to Sluss that he still harbored feelings for his ex, Madison Prewett, just two months afterward. The couple parted ways in January 2020, but the breakup was not aired until March of the following year.

During their separation, Sluss expressed to Peter, “All I’ve ever wanted is someone to fully reciprocate the love I offer them.” He felt that Peter had taken his first engagement from him, a loss that occurred due to trust placed in him. This was something he had been continually asking of Peter.

Kelley Flanagan

During the 24th season of “The Bachelor”, both Flanagan and Peter crossed paths, with Flanagan ultimately finishing in fifth position. The duo revealed their relationship status in May 2020, but called it quits by December of the same year. They reconnected again in August 2022, only to part ways once more in April 2023.

Flanagan and Peter were spotted together at Coachella in 2025.

Brook Sill

Peter publicly revealed his relationship with actress Brook Sill on Instagram in June 2025, stating “Worth the wait 😊”. The former star of “The Traitors” identified Sill, known for her role in “Stranger Things”, in both the post’s caption and the image itself.

On “The Ben & Ashley I. Almost Famous” podcast on iHeartRadio, Peter shared that following his departure from New York and return to Los Angeles, he encountered someone very special.

For the past four years, I’ve been in New York, and during that time, my relationship with Kelley Flanagan had some ups and downs, but for the most part, we were separated. I was mostly single, and it’s no secret that I’ve always desired a committed relationship. However, I wouldn’t push anything; I’d let things happen naturally. Peter clarified that he first met Sil on the day he returned to the city.

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2025-06-29 05:53