Inside Madison LeCroy's Relationship History

Let's be honest — Madison LeCroy's relationship history is pretty complicated. The reality star shot to fame on "Southern Charm," thanks to a scandalous love triangle with co-star Austen Kroll, and ever since then, her tumultuous love life has become some serious tabloid fodder. The Charleston, South Carolina, hairdresser and makeup artist has made no secret of the fact that she'd like to walk down the aisle again, telling Us Weekly in August 2019 that she was "in no rush" but would "possibly" consider another wedding. 

Madison has indicated that she doesn't exactly go looking for love, but she might be open to it. "I don't know how that's going to go with the world the way it is, and dating and things like that. So, we will see if I get out of the house," she told Us Weekly in December 2020. "I think I'm okay. ... I'm not going to rush it. I think when you look for it, it's when you don't find it."

But just who has Madison welcomed into her life, both in front of and away from the cameras? Read on to find out.

Let's start by throwing it back to 2010, when a young Madison LeCroy tied the knot. Pre-fame, the South Carolina native was just 20 years old when she wed her hometown sweetheart, Josh Hughes. The twosome seemed pretty happy, despite being young when they wed, and they appeared to have it all, welcoming their first and only child together two years later, a son named Hudson (via The Daily Dish).

Not much is known about their time as a couple, and both appear to have remained tight-lipped in public about their former relationship, but Madison has shared how becoming a mom changed her perspective on life. "Having Hudson has definitely pushed me to want to be successful," she admitted during the Season 7 premiere of "Southern Charm" (per The Daily Dish). "I mean I have a kid, so I don't have a choice to be lazy."

But, sadly, things between Madison and Josh Hughes just didn't work out...

In the words of southern superstar Dolly Parton, it was D-I-V-O-R-C-E for Madison LeCroy and Josh Hughes. The former couple doesn't appear to have spoken much about why they went their separate ways (Hughes seems to prefer to keep his private life under wraps, unlike his famous ex), but Madison has confirmed that they split after five years of marriage when their son, Hudson, was 3 years old (via The Daily Dish).

Madison opened up about how she has worked hard with her ex to make sure they're both there for their son. She explained on the "Southern Charm" Season 7 premiere in October 2020, "I had Hudson when we were 22. And we divorced when Hudson was 3 years old. And we do co-parenting, so we're 50 percent on [and] 50 percent off" (via the Daily Dish). But things weren't always smooth sailing after their split. "It's been hard being a young single mom and there have been times where I didn't have it together. It's like I'll leave a client sitting in a car. I'll run to go get him and then we come right back," Madison added.

Though he's yet to make any kind of major appearance on the show, Josh Hughes reportedly still resides in South Carolina near Madison and their son when he's not working in the Washington, D.C. area, surely making things easier to split custody right down the middle.

It was actually because of her love life that the world became familiar with Madison LeCroy. The star found fame on Bravo's "Southern Charm," making her debut as a guest star in 2015 for Season 2 and reappearing in 2016 for Season 3. But we really got to know Madison when she had her position upgraded to a "Friend" role for Season 6 of the reality show in 2019. Fans learned all about the ins and outs of her relationship with main cast member Austen Kroll. The two first started dating in January 2018, when they met through Naomie Olindo.

One of Madison's earlier and most explosive storylines saw her accuse Austen of cheating after she, apparently, walked in on him with two women. Madison and Austen got into a seriously heated argument after she claimed she found one of the women's underwear in his bedroom, and the very candid video of the fallout went viral.

Austen went on to address the controversy in May 2019, telling Entertainment Tonight, "I guess what I can say is that was very early on [in our relationship]. [That was] Madison and I trying to figure out what we were. We both hadn't done the, you know, 'you're my girlfriend, and you're my boyfriend' talk, right?" Madison also addressed the clip in an Instagram comment, writing that they "chose to forgive, forget and move forward with a fresh start" (via Bustle).

Despite the, erm, controversial way we got properly introduced to Madison LeCroy on "Southern Charm," she and Austen Kroll seemed to be going strong for awhile after their infamous video found its way online. Well, you could say it was good until it wasn't, as the couple's relationship was again hit with allegations of a third person being involved.

Their drama played out on the show when they hit a tough spot in the May 2019 episode, "Slide Into Your DMs Like...," which saw Madison accused of sending flirty messages to another man. Cast mate Craig Conover claimed that Madison had asked a friend to send a message to Danni Baird's boyfriend, Gentry Todd Radwanski, because Madison was interested in him. Craig then joined forces with Shep Rose to break the news to Austen, who called Danni to get the details.

During a very candid phone call with her boyfriend, Madison initially denied doing anything wrong, but she eventually confessed that she did, in fact, slide in to Gentry's inbox with that now infamous DM. The truth ended her relationship with a livid Austen, and in pretty dramatic fashion.

The drama was much talked-about by fans of the show, and it led to some pretty public mudslinging between Madison and Danni. Both took to social media to leak the alleged DMs, thus sparking a big feud.

Despite all the drama that ensued from the Instagram DM episode, Austen Kroll and Madison LeCroy just couldn't stay away from one another for long. Austen opened up about the status of his and Madison's relationship in an interview with Us Weekly, where he confirmed that the two had rekindled things.

Austen confessed that he and Madison ended up sleeping together when the "Southern Charm" cast took a trip to Colorado. He shared that they'd been in contact a little before the cast packed their bags for the group vacation, despite their breakup, but hadn't really been face to face. "We hadn't really seen each other much, so I was kind of nervous, excited to see her because we were going to be on a trip with our friends so if we can't act right here, then where can we act right?" he said. Austen assured Us Weekly that there was more to come from the development: "You have most certainly not seen the last of Austen and Madison."

And he wasn't lying. The twosome's relationship continued to play out in front of the cameras during Season 6, with the exes repeatedly getting pretty flirty. Things between the two were tested in Season 6, Episode 12, "Who Put The Mad In Madison," but the couple appeared to be all but back together by the following episode, "Outfoxed."

It was never going to be that easy, was it? Following the Season 6 finale of "Southern Charm," it seemed as though Madison LeCroy and Austen Kroll's relationship had hit another snag. As a few questions over the actual status of their relationship arose from fans, Madison revealed where she stood with her on/off boyfriend during an August 2019 interview with Us Weekly.

Could Austen Kroll be "The One" for Madison LeCroy? "Maybe, who knows," Madison responded. She appeared to confirm they were off again, suggesting work had gotten in the way of their rekindled love. "Austen and I's relationship is complicated, obviously. He has said that multiple times. I think right now he's focusing on his beer, which is so great. I'm not trying to be in any way ... I guess I would say just a distraction," she said. (Austen founded King's Calling Brewing Co.)

Madison suggested a chance at yet another reconciliation, though, telling Us Weekly, "I don't want to say that we wouldn't revisit this, because we do feel a type of way about each other." And it sounded like there was no bad blood, despite another apparent breakup. "I love the fact that he has dimples. That's obviously one of the first things I see. I like how tall he is. I love his personality," Madison said of her co-star. "He just makes you feel very welcome, you know? It's just easy, I guess." Is it?

Never apart for long, the spooky season saw Madison LeCroy and Austen Kroll reunite. And we don't just mean reunite, we mean reunite in such a serious way that they rocked their couple's Halloween costume. Now that's serious.

Yep, the two confirmed they were very much back on via Instagram on October 31, 2019, when Austen shared snaps of them dressed up as Marilyn Monroe and John F. Kennedy. The two looked pretty happy together in the photos, with Madison playfully pulling on Austen's tie as they both laughed, before they flashed their pearly whites for a selfie as Madison touched her man's face. "'If not us, who? If not now, when? -JFK' —AFK," he wrote in the caption.

The following month, Austen confirmed they were back on during an interview with their favorite outlet, Us Weekly, and he had a good sense of humor about their rollercoaster relationship. "This week, I'm doing well with Madison. Next week, I'll let you all know," he teased. "I tried to go our separate ways. Madison has been a person for me for a long, long time. It's hard to walk away from someone like that. She really is a hell of a woman. She's got it going on. I find it hard to walk away from her." Spooktacular!

As for what their co-star Craig Conover made of it all? Well, Craig seemed pretty much over the whole Madison/Austen romance thing, really.

Just as it all seemed to be going well, it was over. Yep, the rollercoaster that is Madison LeCroy and Austen Kroll came to an end for a (seemingly, but we'll see) final time when Madison confirmed in December 2020 that they'd broken up again. It was Us Weekly with the exclusive once more, with Madison telling the outlet, "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."

As for the straw that seemingly broke the camel's back? Well, Madison shared that they spent a little bit of quarantine time together amid the coronavirus pandemic, which, unfortunately, didn't exactly strengthen their relationship. "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," she said. Madison also revealed that spending even that short amount of constant time together made them realize they were on "different wavelengths."

Austen then told Us Weekly that same month that seeing their relationship unfold on "Southern Charm" only added fuel to the breakup fire. He confessed that they actually split a few months before the news broke. He revealed they hadn't spoken in two weeks, adding, "It's like I cut off my addiction cold turkey. ... It just hasn't been easy."

Love triangle! Or should we say square? Things got messy in December 2020 when Austen Kroll was spotted with "The Hills" star Kristin Cavallari. The two were spotted spending time in Nashville together alongside Austen's "Southern Charm" co-star, Craig Conover (via People).

Fast-forward a month to January 2021, and Austen Kroll and Kristin Cavallari's exes, Madison LeCroy and Jay Cutler, sparked romance rumors of their own. Us Weekly reported that the two supposedly had a "new, flirty thing" amid Jay and Kristin's divorce. An insider claimed it was "nothing serious" but noted that Jay and Madison were "having fun getting to know each other."

Well, not surprisingly, this one kind of blew up. None of the involved parties seemed too thrilled about the apparent partner swap, with things getting tense during the "Southern Charm" Season 6 reunion. Austen denied dating Kristin and claimed Jay didn't message Madison first, though she claimed he did and even pulled up alleged messages from the retired football player (via The Sun). Madison had previously shared message screenshots on her Instagram Story alongside a snap of herself and Jay with the caption, "Too bad it didn't work out."

Things turned sour between Madison and Jay in another alleged message exchange she shared. The person purported to be Jay called the situation a "mess" and suggested they be respectful of one another, which Madison countered by saying she was "disgusted by this whole situation."

Amid all the now-infamous Jay Cutler/Austen Kroll/Kristen Cavallari drama, Madison LeCroy proved she does have at least one ex in her corner. For years, the identity of her former husband, Hudson's father, was kept a secret as "Southern Charm" fans tried desperately to find out who the man was. 

Well, that long-standing mystery was solved in January 2021, when Madison seemingly unveiled her husband to the world for the first time in any kind of major way via her Instagram Stories.

The star shared a snap of Josh Hughes with a blue cape around him in what appeared to be her salon, confirming they're still on good terms as she gave him a hair cut. Hughes could be seen smiling at the camera as Madison captioned the update (via Page Six), "When your ex husband still trust[s] you with their hair."

Madison didn't mention Josh's name or tag his account, suggesting that the father of her son likes to stay a little more under-the-radar, though the upload made it pretty clear that they're still close for the sake of co-parenting their son.

Moving swiftly on from Jay Cutler, Madison LeCroy's name was also in the headlines in January 2021 for another juicy love life drama. Shortly after everything with the football star played out, Madison was romantically linked to another athlete — Alex Rodriguez. In the scandal heard around the world, social media was ablaze with rumors suggesting the reality star allegedly had some kind of dalliance with A-Rod, despite his engagement to Jennifer Lopez.

It all started when Madison was accused during the Season 7 "Southern Charm" finale of being involved with someone host Andy Cohen described as a "married ex-MLB player" (via New York Post). Madison admitted she spoke to the unnamed man via Instagram but denied going to Miami to meet him, so Craig Conover called her a "f*cking liar" and a "homewrecker," alleging that Madison and A-Rod had gotten intimate in video chats.

As tongues wagged that it was A-Rod, Madison told Page Six she'd "never met up" with him, but they'd "spoken on the phone." Madison said she and A-Rod had "never been physical" and claimed he'd "never physically cheated on his fiancée with me." "Southern Charm's" Shep Rose spoke about the drama to Us Weekly, claiming a non-disclosure agreement was signed.

As for Rodriguez's take, his rep told the Daily Mail in May 2021, "I'm not sure who's looking to benefit from these types of rumors and false stories. They are factually incorrect."

It wasn't too long after the rumors swirled about Madison LeCroy and Alex Rodriguez that the baseball star's relationship with Jennifer Lopez was all but over. In March 2021, Page Six ran the blaring headline, "Jennifer Lopez and Alex Rodriguez broke up over Madison LeCroy scandal," with an insider alleging the two called off their engagement after four years together partly because "Jennifer was really embarrassed by it."

However, Lopez and Rodriguez denied the split and claimed they were "working through some things" (per Sky News), staying together a few more weeks before officially breaking up in April 2021. They told Today they "realized [they] are better as friends."

After splitting from J-Lo, Rodriguez was supposedly interested in pursuing a relationship with Madison and purportedly reached out to her, sources told The Sun. But it seemed like she lacked southern charm in her response. Madison supposedly "rolled her eyes and ignored him," according to the insider, who added, "She's completely over it." Sounds like a swing and a miss for A-Rod...

Madison also appeared to joke about the entire scandal to (who else?) Us Weekly in June 2021, saying the world was "welcome" for Lopez reuniting with her former fiance, Ben Affleck. "I had nothing to do with why [Lopez and Rodriguez] split, and I think everybody knows that. And if you don't know that, then that's just ridiculous," she added.

Moving on! Madison LeCroy seemed ready to put the months of scandal behind her in June 2021 when she went Instagram official with her new man. Madison looked loved-up during a trip to Lake Tahoe in a few vacation snaps she shared of the couple on a boat trip, including a black and white shot of her kissing her new boyfriend. Seemingly learning from the mistakes of the past when it comes to public romances, Madison didn't confirm his name or tag him.

The snaps caused quite the stir, with speculation going to the next level because of a very interesting-looking band on her left-hand ring finger. An engagement ring, maybe? Well, no. She shut down that speculation while chatting with her friend, The Dipp's Samantha Bush, via Instagram DM. "You remember when Venita [Aspen] and I went and got the love rings... well now everyone thinks I'm engaged," Madison wrote, confirming it wasn't an engagement ring.

They may not be betrothed, but Madison and Mystery Man were still going strong as of September 2021, when she shared cozy pics of them on a boat. A month before that, she hinted that things were serious by borrowing a line from "The Bachelor" when she uploaded an Instagram photo of them sipping champagne in the Maldives alongside the caption, "Will you accept my final [rose]."

Let's just hope these two last longer than most Bachelor Nation couples.