Madison LeCroy’s Journey to Love: A Complete Dating History, From Past Romances to Husband Brett Randle and Her Pregnancy Announcement
Southern Charm star Madison LeCroy is once again making headlines, this time with joyful news: she’s pregnant with her second child! This marks her first baby with husband Brett Randle, a significant milestone in her captivating life. The reality television personality, known for her vibrant presence and candid approach to relationships, shared the exciting news on Instagram on Thursday, February 6, posting a photo of a positive pregnancy test and writing, “And just like that … our world is changing in the most magical way! ✨” at 34 years old.
Before finding enduring love with Brett Randle, Madison navigated a series of high-profile relationships and “situationships” that often played out in the public eye, involving notable figures like baseball legend Alex Rodriguez and former NFL quarterback Jay Cutler. Her journey through romance has been a rollercoaster of dramatic highs and lows, a staple of her reality TV tenure. Let’s delve into Madison LeCroy’s complete dating history, exploring the pivotal relationships that have shaped her path to finding happiness and expanding her family.
Josh Hughes
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Madison LeCroy’s first foray into marriage began in 2010 when she married Josh Hughes at the young age of 20. Their union welcomed a son, Hudson, in November 2012. Madison often shares glimpses of Hudson on her social media, showcasing her devotion as a mother. However, the couple’s relationship ultimately concluded in 2015, with their divorce marking a new chapter for Madison. This early marriage and subsequent divorce significantly shaped her perspective on relationships and her fiercely independent attitude. She has frequently expressed her self-reliance, emphasizing that she doesn’t “need a man,” a sentiment that resonated with many of her followers and reflected her determination to navigate life as a single mother.
Austen Kroll
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Madison LeCroy’s turbulent relationship with her Southern Charm co-star, Austen Kroll, became a central storyline when she made her debut on the Bravo series in season 6. Their on-again, off-again romance spanned from 2018 to 2020, captivating viewers with its passionate highs and dramatic lows. The couple’s dynamic was frequently a topic of discussion among fans and castmates alike, often characterized by heated arguments and emotional reconciliations. They finally called it quits for good in December 2020, with Madison confirming the breakup to Us Weekly, famously stating, “We are not together right now. I am 1,000 percent single, and so is he. So, ladies, if you want him, you can have him.”
Reflecting on their split, Madison later shared that the COVID-19 pandemic and subsequent quarantine played a significant role. She explained, “I definitely think that quarantine was either gonna make it or break [our] relationship, and unfortunately, we did not come out stronger. We weren’t even in quarantine together. We did for a short period of time, and then I think we both realized that maybe there was just too many things that had happened in the past for us to actually play house for 14 days or whatever it was.” Austen, for his part, openly labeled their relationship as “toxic.” During the Southern Charm reunion in early 2021, he further elaborated on his heartbreak, expressing, “My heart just broke over and over again. I saw what all my friends have been telling me for years: She does not f–king care about me and she never f–king has.” Their tumultuous romance remains one of the most memorable relationships in Southern Charm history.
John Pringle
In season 7 of Southern Charm, which aired in the fall of 2020, newcomer John Pringle quickly developed a strong infatuation with Madison LeCroy. At this time, Madison was still technically involved with Austen Kroll, although their relationship was rapidly approaching its final conclusion. Their on-screen flirtation sparked considerable tension, particularly with Austen, and became a significant plot point. However, Madison was quick to define the nature of her connection with Pringle. By December, she clarified to Us Weekly that she intended “on keeping him in the friend zone,” effectively shutting down any prospects of a romantic relationship.
John Pringle later expressed his feelings about the situation, telling Entertainment Tonight that he felt he was used as “a bit of a pawn” in Madison’s ongoing drama with Austen. He suggested that Madison strategically leveraged their flirtation to provoke a reaction from Austen, highlighting the intricate and often manipulative dynamics that characterized the relationships on Southern Charm. Pringle’s perspective shed light on the calculated nature of some of the reality show’s storylines, where personal feelings could easily become intertwined with the demands of television. Despite the on-screen chemistry and the dramatic impact, Madison and John’s connection never blossomed beyond a brief, televised flirtation.
Jay Cutler
The rumored romance between Madison LeCroy and former NFL quarterback Jay Cutler quickly spiraled into a highly public and petty feud in late 2020. This speculation arose nine months after Cutler’s split from reality star Kristin Cavallari, with whom he shared seven years of marriage and three children. The situation was further complicated by Kristin’s own highly publicized outings with Madison’s ex, Austen Kroll, and his Southern Charm co-star Craig Conover in Charleston that October. The intertwining social circles and past relationships created fertile ground for drama.
The controversy ignited in November 2020 when Madison left a provocative comment, “See y’all soon,” on an Instagram photo of Jay Cutler with Shannon Ford, a former employee of Kristin Cavallari with whom Kristin had a public falling out on her reality show, Very Cavallari. The stakes escalated when Madison reportedly mocked Kristin’s Instagram Live session with Austen, seemingly adding fuel to the fire. In response, Jay and Kristin appeared to present a united front, sharing a joint photo on social media with the pointed caption: “The world is full of users. 10 years. Can’t break that.” This seemingly subtle jab was widely interpreted as a direct reference to Madison.
Undeterred, Madison LeCroy fired back with “receipts,” posting alleged screen grabs of past conversations with Jay Cutler. In these messages, she claimed that Cutler had been the one to pursue her, vehemently defending herself against accusations and implying that she was being unfairly targeted. The social media spat captivated tabloids and fans, adding another layer of intrigue to Madison’s public image. Amidst the ongoing drama, Kristin Cavallari clarified in December 2020 that her relationship with Austen Kroll was strictly platonic, attempting to diffuse some of the tension. This entire saga underscored Madison’s ability to remain at the center of media attention, even when not directly on Southern Charm.
Alex Rodriguez
Madison LeCroy’s most significant and widely discussed “situationship” came to light in early 2021, linking her to former MLB superstar Alex Rodriguez. The rumors of a connection between the Bravo star and A-Rod emerged shortly after her drama with Jay Cutler, further cementing her status as a magnet for high-profile gossip. The scandal began to unfold dramatically during part one of the Southern Charm season 7 reunion in January, when co-star Craig Conover directly accused Madison of flying “to Miami to f–k an ex-MLB player.” Given Rodriguez’s prominent residence in Miami and his legendary status as a New York Yankees player, the accusation immediately pointed to him, sparking a media frenzy.
In February, Madison addressed the swirling allegations in an interview with Page Six. She confirmed that she had been communicating with Alex Rodriguez via FaceTime, but adamantly maintained that they had never met in person. “He’s never physically cheated on his fiancée with me,” Madison stated, referring to Rodriguez’s then-fiancée, pop icon Jennifer Lopez. She also added, “I don’t want anything bad for his family, or for mine. We are definitely innocent in this.” A spokesperson for A-Rod echoed this sentiment, asserting that the businessman had never met Madison, while Jennifer Lopez herself remained notably silent on the matter. The controversy, fueled by reality TV confessions and high-profile denials, cast a shadow over both their public images and was a major talking point in celebrity news for weeks. This incident proved to be one of Madison’s most memorable and controversial moments in the public eye, showcasing the intense scrutiny that comes with being a reality television star.
Brett Randle
After a series of public romances and dramatic entanglements, Madison LeCroy finally found her true match in Brett Randle. The couple’s relationship first became Instagram official in June 2021, when Madison shared a sweet photo of them cuddling on a boat, signaling a new, more stable chapter in her romantic life. Their initial meeting reportedly occurred during a girls’ trip Madison took to Arizona, a chance encounter that blossomed into a deep connection. The romance progressed swiftly and privately, a stark contrast to her previous public relationships. By October 2021, Madison excitedly confirmed their engagement to Us Weekly, sharing her joy about finding a partner who offered stability and genuine happiness. The couple officially tied the knot in an intimate ceremony in November 2022, marking a peaceful and joyful conclusion to her quest for love.
However, their journey together has not been without its challenges. In December 2024, Madison revealed a deeply personal struggle on an episode of Southern Charm: Brett had been diagnosed with thyroid cancer in the fall of 2023. This devastating news came shortly after the couple had shared their intentions to start trying for a baby in November. Madison emotionally recounted the ordeal, explaining that after the successful removal of a “three-centimeter nodule,” Brett was declared cancer-free, but his recovery involved “complications.” The experience understandably took a toll on Madison, who admitted, “Some days I just want to scream,” describing how anything, including innocent questions about having children, could trigger her emotions. She openly shared the impact on their family planning, stating, “We were just kinda starting to plan, but that’s on pause for now.”
Through it all, Madison and Brett’s bond only strengthened. The challenges they faced together, particularly Brett’s health battle, deepened their commitment and love. Now, in February 2025, a mere two months after sharing their difficult journey, the couple announced the joyous news of their first child together! This pregnancy is a testament to their resilience, hope, and unwavering love, marking a beautiful new beginning for the Randle family. Madison’s path to motherhood with Brett, following her earlier experience with her son Hudson, highlights a profound and fulfilling new chapter in her life, celebrated by fans and loved ones alike.
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