Every Relationship She’s Been In – Hollywood Life

We’ve chronicled Madison LeCroy’s dating history. Learn about the relationships she’s been in and the stars she’s been linked to!

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 up with. — We did the research so you don’t have to. Here’s a full break-down of Madison’s relationship history:

Josh Hughes 

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. 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 to be whole.

Austen Kroll 

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-off from 2018-2020, before they split for good in December. Madison and Austen later admitted that quarantine, due to the COVID-19 pandemic, played a part in their breakup. Additionally, Austen labeled the relationship as “toxic.”

During the Southern Charm reunion in early 2021, Austen 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 

John Pringle & Madison LeCroy. (Photo credit: BRAVO)

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, romantically. Madison and John’s fling played out on the show in the fall of 2020. aired in the fall of 2020. In December, Madison later 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.

Jay Cutler 

Madison LeCroy & Jay Cutler. (Photo credit: BRAVO/Shutterstock)

This one turned petty, fast. In early January, rumors surfaced that Madison and Jay Cutler were casually dating, but there was not proof. Both Austen and their Southern Charm co-star Craig Conover even accused Madison of having some sort of connection to the former NFL quarterback — but still, no proof. Things escalated when Madison took to social media to share alleged screenshots between the model and Jay.

Prior to sharing her text messages, LeCroy posted a photo on her Instagram Story on Saturday of herself drinking a large margarita, writing on the snap, “Cheatin.” Then on Sunday, the mother of one shared a video of herself talking to the camera while sitting outside and saying, “It looks to me like I’m going to have to drop some receipts. Hate to do that… but.”

Following LeCroy’s negative video directed at Cutler’s estranged wife, the former athlete and Cavallari, who share three children, posted a photo together, captioning it, “The world is full of users. 10 years. Can’t break that.”

LeCroy clapped back at the Instagram post by releasing her alleged text messages with Cutler the same month, ending the short romance. In the screenshots, it appeared that the former Chicago Bears player pursued LeCroy, visiting her in South Carolina. “You reached out to me … Your intentions may have not been pure but that might be you projecting. I’ve never said anything about Kristin nor would I,” LeCroy texted him. “I came into this honestly with good intentions. I want no part of being involved in a payback or drama. But you initiated and pursued. If you weren’t interested in something real you shouldn’t have [redacted] with me.”

Alex Rodriguez 

Alex Rodriguez. (Photo credit: Shutterstock)

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 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. Although Madison denied the latter claim, her other co-star, Shep Rose told Andy Cohen during a March 15 radio interview that Madison had to sign an NDA because she was direct messaging with Alex on social media.

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