Southern Charm‘s Madison LeCroy has been making headlines for more than her parties on the hit Bravo show. More recently, the reality star has found herself in some situation-ships (if you will) with high-profile stars, including Alex Rodriguez and Jay Cutler. Between the various reports and down right random rumors about her love life, it can be hard to keep track of who she’s dating. — We did the research so you don’t have to. Here’s a full break-down of Madison’s relationship history:
Madison has been married. In 2010, she tied the knot with Josh Hughes (pictured in the second slide of the above Instagram post) at age 20. Two years later, in November 2012, they welcomed their son, Hudson. Madison and Josh eventually called it quits in 2015, as reported by Us Weekly. The single mom has maintained a fiercely independent attitude ever since — having noted on more than one occasion that she doesn’t need a man.
Madison struck up a romance with her Southern Charm co-star Austen Kroll in season 6 — when she made her debut on the Bravo series. They dated on and off from 2018-2020, before they split for good in December, having confirmed the breakup to Us Weekly. “We are not together right now. I am 1,000 percent single, and so is he,” she at the time, adding, “So, ladies, if you want him, you can have him.”
Madison later admitted that quarantine, due to the COVID-19 pandemic, played a part in their breakup. “I definitely think that quarantine was either gonna make it or break [our] relationship, and unfortunately, we did not come out stronger,” she explained. “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.”
For his part, Austen labeled the relationship as “toxic.” During the Southern Charm reunion in early 2021, Austen further discussed his relationship with Madison and said, “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.”
John Pringle joined Southern Charm in season 7, and became smitten with Madison — who as still involved with Austen at the time, but nearing the end of the road with him, romantically. Madison and John’s fling played out on the show in the fall of 2020. In December, Madison told Us Weekly that she planned “on keeping him in the friend zone.”
For his part, Pringle later told Entertainment Tonight that he felt he was a “bit of a pawn” in Madison’s attempt to make Austen jealous. “She knows what she’s doing. You know, what strings she’s pulling to get a reaction out of him, and it usually works,” he explained.
This one turned petty, fast. In late 2020, rumors surfaced that Madison and Jay Cutler were casually dating — nine months after his split from Kristin Cavallari, following seven years of marriage and three kids together. In that time, Kristin made also headlines for hanging out with Austen and his Southern Charm co-star Craig in October 2020, in Charleston.
The next month, in November 2020, Madison raised eyebrows when she left a comment on Jay’s photo with Shannon Ford, writing, “See y’all soon.” Shannon is one of Kristin’s former employees, who she had a nasty falling out with on her Very Cavallari reality show.
Things escalated when Madison went on Instagram Live and mocked Kristin’s Live that she previously filmed with Austen. After that, Jay and Kristin seemed to put on a united front when they shared a photo together on social media with the caption:“The world is full of users. 10 years. Can’t break that.”
The drama didn’t end there. Madison fired back by pulling out receipts, in the form of screen grabs, she had saved from previous conversations with Jay. In the alleged messages, Madison claimed that Jay was the one who pursued her and even defended herself over her posts about Kristin. In December 2020, Kristin clarified that she’s just friends with Austen.
Madison’s most recent involvement with a big-name star came soon after her saga with Jay. In early 2021, it was reported that Alex had formulated an online relationship with Madison, following rumors of a connection between the pair. In February, the Bravo star told Page Six that while she was communicating with Alex via FaceTime, the two had never met in person.
“He’s never physically cheated on his fiancée with me,” Madison said last month, adding, “I don’t want anything bad for his family, or for mine. We are definitely innocent in this.” At the time, a spokesperson for A-Rod said the businessman had never met Madison. Meanwhile, Alex’s fiancee, Jennifer Lopez has remained silent about the situation.
The scandal first came to a head in January, during part one of the Southern Charm season 7 reunion when Craig accused Madison of getting on a plane and flying “to Miami to f–k an ex-MLB player.” For context, Alex has a home in Miami where he spends much of his time, and it’s no secret that he’s one of the most decorated players in New York Yankees history.