Southern Charm's Madison LeCroy's Complete Dating History

Madison LeCroy has become a fan-favorite on Southern Charm thanks to her tell-it-like-it-is attitude and heartwarming relationship with her son, Hudson. With Season 10 premiering in early December, the series' trailer shows Madison navigating her marriage to chief firefighter Brett Randle and getting revenge on newbie Jarrett "JT" Thomas, who, shockingly, resigned from the show.

Madison's journey with the charmers began in Season 6, when she was Austen Kroll's love interest. And fans all know how messy their relationship played out. When it comes to other romantic partners, Madison has seen her fair share of rumors—particularly allegedly hooking up with Jennifer Lopez's former fiancé, Alex Rodriguez.

The reality TV star has been happily married to Brett since 2022, but fans of Southern Charm are extremely interested in her complete relationship history, including whom the father of her son is.

6 Madison LeCroy Shares Son Hudson With Her Ex-Husband, Josh Hughes

Madison LeCroy made her first appearance on Southern Charm in Season 6, where fans learned that she was a mother to a son named Hudson from her first marriage. According to Us Weekly, Madison was only 20 when she married Josh Hughes, a certified personal trainer and recruiter, in 2010. Two years later, they welcomed their son, Hudson, into the world.

Madison and Josh separated when Hudson was 3 years old. The former couple split time with Hudson 50/50, with Madison telling the outlet, "And we do coparenting, so we're 50 percent on [and] 50 percent off."

Josh has not been seen on Southern Charm, but it appears that he and Madison have a healthy relationship for the sake of their son.

5 Madison Appeared As Austen Kroll's Love Interest In Season 6

Madison was dating her Southern Charm co-star Austen Kroll in Season 6 in 2019. However, according to photos on her Instagram, the two began dating the previous year. Their last photo together is the one above in which she captioned it, "ILY from my head to my toes."

Madison and Austen had an on-again, off-again relationship that ended in 2020. Southern Charm viewers watched them bicker and argue constantly, even when it wasn't even about their relationship. The following year, Madison told Bravo why the two just didn't work:

"I would say Austen and I, you know, the relationship was actually pretty good in the beginning. Especially before we put it on international television. That, I think, changed a lot of things for us. We had no privacy. Any fights, any drama, everybody knew about it."

Season 10 shows Madison and Austen on good terms, which may shock a few fans. During one of her Amazon Live shows, Madison even insisted that she'd invite her ex to a hypothetical Friendsgiving. "I think after five years of time, it’s like you just gotta grow up. We’re adults, we work together, so yeah."

4 John Pringle Believed He Was A "Pawn" In Madison's "Relationship Chess"

John Pringle came onboard in Season 7, and he had his eyes on Madison as she and Austen were on the outs. In fact, even Patricia Altshul encouraged John to pursue something romantic with Madison, but it didn't get anywhere. In an interview with ET, John revealed that Madison just used him to get back at Austen.

"I just don't necessarily subscribe to the fact that Madison is interested in me at all. I think I was a bit of a pawn and I think she is a master player of relationship chess."

He continued, "She knows what she's doing. You know, what strings she's pulling to get a reaction out of him, and it usually works. Like, they're usually the reaction she wants and I'm a victim of that in relationships, too -- or I do it. You know, I've seen it before, I've been a part of it."

3 Madison's Short-Lived Romance With Jay Cutler Was Messy

Madison and former NFL quarterback Jay Cutler "had a thing" at the start of 2021, just several months after he and Kristin Cavallari announced their divorce. According to Us Weekly, after Madison allegedly shared a "negative video directed at" Kristin, the Laguna Beach alum hit back at the Southern Charm star by sharing a photo with Jay and captioning it, "The world is full of users. 10 years. Can’t break that."

Madison then proceeded to share her private text messages between her and Jay on Instagram. The messages showed that Jay pursued her and even bought a flight to see her in South Carolina. Madison also shared a selfie with Jay, proving that they had spent time together.

2 Madison Was Called Out By Her Castmates For Her Alleged Affair With "Married Men, Ex-MLB Players"

Things got really heated during the Southern Charm Season 7 reunion when Craig Conover accused Madison of “flying around the country sleeping with men, married men. Ex-MLB players." Madison quickly denied the allegations, but she did admit that she and the mystery MLB player did FaceTime, but never physically hung out.

During that time, it was widely speculated that Madison had an affair with former Yankee star Alex Rodriquez, who was engaged to Jennifer Lopez.

The following month, Madison doubled down on her statement, telling Page Six, "He’s never physically cheated on his fiancée with me. [It’s] never been physical … never had any kind of anything. Just an acquaintance.”

1 Madison Married Brett Randle After A Whirlwind Romance

Madison and Brett Randle had dated for only seven months when the latter proposed to the reality star in October 2021. Madison shared with Us Weekly that her soon-to-be husband had a lot of help creating the perfect proposal thanks to her son, Hudson.

"I think my son looks up to him in so many ways. It's because he's such a good influence and not only on him, but even me as a person. He makes me want to be like the best version of myself."

In November 2022, Madison and Brett married in a small ceremony in Mexico. During the show, Madison spoke about how they maintained a strong relationship with Brett, traveling back and forth for work, as he is a chief firefighter in California.

Speaking to E! News in October, she revealed that she and Brett are "trying" to expand their family. Fans will get a chance to see more of their relationship in Southern Charm Season 10.