‘Southern Charm’ alum Thomas Ravenel’s dating history: Kathryn Dennis, Olivia Flowers and more hooku

Thomas Ravenel has quite the dating history.

When the “Southern Charm” alum wasn’t involved with a co-star, he made sure to film with whomever he was romancing at the time.

The former politician starred on the Bravo reality series from Season 1, which premiered in 2014, until Season 5.

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In 2018, he got fired amid legal troubles following allegations of sexual assault.

Below is a timeline of Ravenel’s love life:

Danni Baird

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Ravenel tried to woo then-castmate Danni Baird during Season 1, but she was not interested in being more than friends.

In fact, Baird — who previously dated Shep Rose — stopped Ravenel from kissing her at the end of their one and only date.

Kathryn Dennis

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Ravenel met Kathryn Dennis during a Season 1 party at Patricia Altschul’s house when she was a college student and he was running for the United States Senate.

Cameras rolled as they fought, made up and even experienced a pregnancy scare.

However, shortly after, Dennis learned she was expecting. They welcomed their first child together, daughter Kensington “Kensie,” in March 2014.

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The pair initially tried to live as a family, but their disagreements got the best of them, so they called it quits.

They briefly got back together in 2015, which is when they conceived their second child. Dennis gave birth to a boy, St. Julien “Saint,” in November 2015.

The duo went their separate ways again in 2016 and entered a messy and seemingly never-ending custody battle, which remains ongoing.

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During the Season 7 reunion, Dennis admitted that she and Ravenel hooked up once in 2020.

“But never again,” she maintained at the time. “That door is closed.”

Landon Clements

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Ravenel met Landon Clements when she was a college student and he was in his mid-30s.

The two got close during Season 3 and eventually went on an awkward date during Season 4.

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Though they both seemed interested in each other at the time, Clements later denied that she and Ravenel were ever romantically involved.

“Thomas and I are really good friends,” she insisted in 2017. “I’ve known him forever-ever. He is just more like a family member — an uncle or a cousin or something. We’ve never crossed those lines, and we never will.”

Ashley Jacobs

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Two years after Ravenel and Dennis broke up, he began seeing Ashley Jacobs, who appeared in Season 5.

The then-couple got into several screaming matches during filming, including one moment when Jacobs called Dennis an “egg donor.”

Ravenel went on to accuse Jacobs of cheating on him, which she denied, and dumped her in 2018.

Heather Mascoe

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Ravenel welcomed a third child, son Jonathon, with Heather Mascoe in June 2020.

At the time of the birth, Ravenel claimed he and Mascoe had previously dated but were just “really good friends.”

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However, six months later, he confirmed they were “happily engaged.”

Shortly after, the pair scrubbed their Instagram pages and unfollowed each other.

During the Season 7 reunion, Dennis said she had not met Mascoe or the new baby but that her kids “apparently” had.

Olivia Flowers

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During the Season 8 reunion, Madison LeCroy claimed that co-star Olivia Flowers once hooked up with Ravenel, but the latter — who is friends with Dennis — denied it and asked whether the former had “pull[ed] that out of [her] fake ass.”

“He’s, like, a family friend,” Flowers insisted at the time.

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However, during the Season 9 reunion in 2024, the topic came up again thanks to frenemy Taylor Green, and Flowers fessed up.

“I was fresh out of college, 20 years old, dumb, drunken night,” she admitted. “One time had a hookup with T-Rav, and I wanted to take it to my grave. Like, who wouldn’t?”

Flowers said she “met Kathryn after it happened,” but Green claimed the former had told her “it was five years ago after baby No. 2.”