The Stunning Transformation Of Kelley Flanagan

When Kelley Flanagan first stepped on the set of "The Bachelor" in 2019, she was a relative nobody. As a recent law school grad working for her family's law firm in Chicago, the brunette had no previous TV experience, as Kelley's LinkedIn page shows. Nonetheless, she went through the "Bachelor" casting process, partially "to learn about the entertainment industry," as she put it in an interview with "Business Unusual." Within months, Kelley's name was making headlines, thanks to her very public romantic connection to "Bachelor" lead Peter Weber (via People).

According to Kelley, this abrupt transition from anonymity to fame was not easy. In an interview with Access Hollywood, the former TV star opened up about how her life has changed after her appearance on The Bachelor: "In terms of how my life has changed post-show, it's a lot. It's a lot. I always tell people that the highs are really high, but the lows hit really, really low." Kelley then went on to describe the mentality that has helped her cope with her newfound fame. "You got to learn how to be comfortable with yourself. You got to learn to try to drown out the noise if you can," she explained.

All of these lifestyle changes ultimately changed Kelley. As she herself admitted to Access Hollywood, "Overall, coming off the show, it's a big transformation."

Kelley Flanagan was once a wild child

Kelley Flanagan is a successful lawyer-turned-influencer; however, the "Bachelor" star has confessed that she wasn't always so put-together. In her interview with Barbara Corcoran on the podcast "Business Unusual," Kelley revealed that she was rebellious in her younger years. "We would do little things back in the day. You know, we would TP houses ... it probably wasn't the best thing to do ... it was playful fun," she explained.

Despite all these shenanigans, Kelley's parents tried to keep her on the right path, she explained. This firm sense of family guidance is one of the reasons that Kelley was able to become successful. In May 2022, she opened up about her upbringing on an episode of "Talking It Out with Bachelor Nation." "One thing my parents tried to ingrain with us was, 'Hey, look, we're not going to do it for you. If you want to be successful in your own right, you better work your a** off and get there,'" she shared. Ultimately, Kelley is grateful for her parents' tough love. As she put it on the show, "I can thank my parents for putting that pressure on [me]."

Kelley Flanagan was a star student

Kelley Flanagan may have been a rebellious teen, but that didn't stop her from becoming an academic powerhouse. For high school, landed a spot at the prestigious Culver Academy boarding school. According to her interview with "Talking It Out," this experience allowed Kelley to develop close ties with people from other cultures. "A lot of my friends have been from the Middle East, or from China, or [from] all over the world. And I was able to do that because my parents did send me to that boarding school," she revealed.

In college, Kelley was able to grow her interest in international leadership. At the University of Alabama, she served as a Global Ambassador for the Semester at Sea program as well as a liaison for the global artisan group Serengetee (per Us Weekly). And these extracurricular activities did not prevent Kelley from earning good grades. She reportedly made the Dean's List for academic excellence before earning a seat at Chicago-Kent College of Law.

All of these impressive achievements may lead some to wonder where Kelley's motivation comes from. The former "Bachelor" contestant admits to holding high expectations for herself from a young age. As she told "Talking It Out," "[My parents] didn't push me. They weren't like, 'You have to go [to boarding school].' I put pressure on myself."

A mystery person nominated her for The Bachelor

Kelley Flanagan's mind-blowing CV may leave some fans wondering why she signed up to go on The Bachelor in the first place. When the show started filming, Kelley was a budding lawyer with a new position at her father's firm. And she didn't necessarily need the media exposure for a career boost. The truth, however, is that Kelley never applied to go on the show at all.

According to the lawyer-turned-influencer, she still has no clue who submitted an application on her behalf. "Someone recommended me [for the show] ... I'm still trying to figure out who it is...I didn't have any 'in' to, like, a producer. I didn't know anyone that worked for the network," she told "Business Unusual."

Because of these dynamics, Kelley was really hesitant about the idea of going on TV. "I wasn't the biggest advocate of the show to start off with," she confessed in a 2021 episode of Off The Vine with Kaitlyn Bristowe. At the time, Kelley was concerned about how the show could impact her professional reputation. As she expressed on Business Unusual, "I was like, what about if something happens and I get a horrible portrayal on the show? ... There was definitely a concern in terms of the law field to come off and ... if I get a bad rap, it could really hurt me."

Peter Weber convinced her to go on The Bachelor

While Kelley Flanagan wasn't 100% certain about going on "The Bachelor," she also wasn't entirely closed off to the idea. "I didn't really want to do this at first. I kept saying there would be a sign from God to tell me if I should do this," she told People

Luckily for Kelley, she didn't have to wait too long for her answer. As Kelley told Off The Vine, while she was attending a friend's wedding at a hotel in Malibu, she spotted future Bachelor Peter Weber in the lobby (via Refinery 29). Kelley approached Peter, introduced herself, and asked him about his time on the show. The two ended up talking for hours and Weber said being on "The Bachelorette" was the "best experience of [his] life."

For Kelley, meeting Peter before filming even started was "a major sign" to go on The Bachelor (via Refinery 29). In fact, Kelley's whole interaction with Peter in Malibu is what convinced her to participate in the program at all, Kelley told Business Unusual

Kelley Flanagan didn't thrive on screen

Kelley Flanagan may have received a "sign" to go on "The Bachelor," but that didn't prevent her from having a hard time during filming. The reality star herself admits that she wasn't exactly a producer favorite. "I think I was told on, like, week 2 that I was not good for TV," Kelley revealed on "Business Unusual." According to Kelley's account, the problem was that she wasn't dramatic enough for the show's producers. "I was close with the girls, and I would try to diffuse a lot of the [dramatic] situations. And you can't have that on a show," she admitted in a 2021 episode of "Chicks in the Office."

Ultimately, these difficulties prevented Kelley from connecting with Bachelor Peter Weber on screen, despite their initial attraction to each other. In an interview with The Viall Files (per E! News), Peter opened up about how the show's environment hindered his relationship with Kelley. "Kelley will be the first one to admit this: Kelley was not good for the show. [She] was not comfortable ever, never felt in her element," he reflected. "I feel like, you know, for what it's worth, I feel like maybe our relationship on the show, it didn't really play out in the best way for us," he continued.

She remained close with Kelsey Weier after The Bachelor

Unfortunately, since Kelley Flanagan's personality didn't translate well to the show's environment, Peter Weber eliminated her one week before hometown dates. The pair had their final conversations during a three-on-one date in Peru, which did not exactly paint Kelley in a positive light.

In the episode, Peter grilled her about her true motivation for going on the show, implying that she went on "The Bachelor" to have a good time and not to find a husband (per Hollywood Life). In the end, Kelley was not able to convince her on-screen beau that she was there for marriage and she left the reality show in 5th place. 

While Kelley was certainly disappointed with her elimination, she didn't let the letdown sour her relationships with the other contestants. Instead, she chose to foster close friendships with the other women from the show. In an interview with "Chicks in the Office," Kelley revealed a deep friendship with the 3rd place finisher from her season. "Kelsey Weier and I talk every single day for, like, hours," she said. The best part is that Kelsey hasn't been afraid to show Kelley a whole lot of love on her social media pages. In one Instagram post, Kelsey even goes as far as to call Kelley her "best friend."

Kelley Flanagan became an influencer and investor

Kelley Flanagan may not have felt comfortable being on TV, but that didn't prevent Bachelor Nation from falling in love with her. According to a report by Bachelor Data, Kelley walked away from the program with close to 200,000 followers on Instagram. As of this writing, that number has climbed to a whopping 784,000 followers. On her personal website, Kelley wrote that this newfound fame allowed her to explore new career opportunities: "After the show, I gained a social media presence and decided to grow my platform while getting involved in this new 'influencer/content creator' industry." 

But Kelley has dared to be more than your average influencer. Instead of simply engaging in brand partnerships, the young entrepreneur decided to dip her toes into the world of investing. "My first investment was with a company called Realm, a smoothie company that creates their recipes from counting macros," she explained on her website. According to Kelley, this initial investment turned out to be a very positive experience. She wrote, "It was a perfect fit being that I've always tried to stay pretty healthy my whole life and wanted to get involved in [any way] that I could!"

Kelley Flanagan briefly dated Peter Weber in 2020

Even as Kelley Flanagan's life evolved after the show, she couldn't seem to stay away from Peter Weber. In 2020, the ambitious career woman ran into her old flame at the Miami Super Bowl (per E! News). The pair started chatting, swapped numbers, and within months, they were in a 100% committed relationship.

According to Peter, this off-screen phase of their love story allowed the pair to get to know each other in a much more genuine way. "We've truly spent probably every single day with each other," Weber divulged in a 2020 exclusive with ET. "I think that is just what has shown us that this is working. It's super just natural and organic."

In the ET exclusive, Kelley couldn't help but agree with her beau. She went on to explain how her time on the show prevented Peter from seeing the real her. "[Peter] didn't even really get to know me that well on the show," Kelley said. "But, like, I saw a lot of compatibility things that added up between him and I. But, he [didn't] necessarily know that. He didn't know me."

Luckily, this didn't stop Kelley and Peter from getting to know each other after the cameras stopped rolling. "For whatever reason, we just didn't really get to know each other super well on the show. It wasn't our cup of tea. But in real life, after, it's just been seamless," Peter told ET.

She moved to Miami alone

In spite of all the hype surrounding Kelley Flanagan and Peter Weber's relationship, the pair broke up just months after they became official. And the timing of their separation was generally surprising for most fans, as the breakup came just a week after Peter announced that he was going to move to New York City with Kelley by his side. "So grateful Kell was on board with the move," he revealed on Instagram at the end of December 2020 (via Cosmopolitan). But by New Year's Eve, the pair had called it quits, according to E! News

Kelley, however, did not let the disappointment of the breakup stop her from moving to a big city. Although she was originally still planning to move to New York post-Peter, the influencer revealed that she was going to Miami instead in an effort to practice self-care. In a November 2021 Instagram post, she wrote, "All jokes aside, this past year has been a rough one with so many re-directions but I am finally committed to Miami this year." The corresponding photo shows Kelley smiling in a swanky new apartment, dangling a set of keys in her hand.

Kelley Flanagan was diagnosed with Lyme disease

From the outside, Kelley Flanagan's life may appear to be picture-perfect, with a blossoming career and a chic new South Florida flat. However, this image doesn't tell the full story. According to Kelley's business page, she was diagnosed with Lyme disease at the end of 2021. Unfortunately, this major health challenge hasn't been easy for the influencer. "It's a blessing and a curse because now I can target why I feel off so often but also means several different lifestyle changes and extensive research on how to help/hopefully cure this," she divulged in an Instagram post.

While Kelley is certainly dedicated to her goal of recovery, the path forward isn't necessarily easy. In an exclusive with Us Weekly, the former reality star confessed that her treatment plan is going to be pretty extreme. "I'm flying to Boston to figure it out and go see the doctors there and just kind of learn how to maneuver it, but it's going to be intense: No carbs, no sugar, an oxygen tank for, like, 30 minutes a day, brainwaves lasers," she told the outlet. Although this medical approach may sound overwhelming, Kelley has expressed a positive attitude about getting through it. "It's going to be extensive, but I'm ready to tackle it," she shared.

Kelley's diagnosis also meant she had to put practicing law on hold, she revealed on "Talking It Out with Bachelor Nation" in May 2022 (via Bachelor Nation). "I might go back into it, just not necessarily with my family's firm. I might do something else with my law degree," she explained. "For right now, I'm not doing law."

Is she back with Peter Weber?

Since late 2021, Kelley Flanagan has been focused on taking care of her health. Nonetheless, the former "Bachelor" contestant hasn't managed to stay out of the spotlight. In August 2022, Kelley once again found herself making headlines after a "Bachelor" fan spotted her strolling through an airport with none other than Peter Weber (via Elite Daily). If that wasn't enough to spark dating rumors, the pair were also photographed together at a Chicago Cubs game, according to ET

The most intriguing part of this whole situation, however, is that neither Kelley nor Peter did anything to stop the rumor mill from flying. If anything, the dynamic duo has been teasing the possibility of a reconciliation. On August 28, Kelley posted a photo of herself in a pink cocktail dress on her Instagram. And when a fan told her that the dress was giving them "impure thoughts," Peter didn't hesitate to comment, "same" (via Us Weekly).

Whether or not the couple is officially dating has not been determined as of this writing. However, Kelley's fans will certainly wish her the best in this next phase of her public life, regardless of her relationship with Peter.