Kristin Cavallari Once Sent Harry Jowsey ‘a Lingerie Photo’ After She ‘Woke Up Horny,’ So He Sent ‘a D— Pic’ Back

Kristin Cavallari is a flirt, and she’s not afraid to admit it!

The reality star, 38, welcomed Harry Jowsey to her live podcast show in Chicago in the June 11 episode of Honestly Cavallari: The Headline Tour, where no topic was off limits. As the pair discussed their sex lives, Cavallari recalled waking up to an NSFW picture from the Too Hot to Handle alum on Instagram.

“I had a feeling,” she joked about the contents of the photo.

“Did you?” Jowsey, 28, replied. “Because it was, like, 7 a.m. as well.”

“It was early! Like, morning wood,” Cavallari then quipped, inciting cheers from the audience.

Cavallari questioned if Jowsey was ready for a relationship given his flirtatious behavior.

Joking that Jowsey is sending “rapid fire d— pics everywhere,” Cavallari wondered how he expects to ever settle down after he said he wanted to be “husband material.” He then told her that she is one of his “selective” few who receive them.

“When you get married, will I be invited to the wedding?” she went on to tease.

“If you’re objecting, for sure,” he poked back.

In her confessional, the Let’s Be Honest host didn’t know how to answer when a producer asked if she had sexual tension with Jowsey. She did, however, explain that she understands him in a way others don’t.

“He has this reputation of sort of being the playboy, not the best rep,” Cavallari noted. “But when you get to know him, he is the sweetest. I’m always open to flirting.”

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Jowsey and Cavallari sent explicit images to each other after the show.

The next day, the banter shifted to texts — but this time, The Hills alum made the first move.

“So this morning, because this is the s— that I do, I sent him this picture,” she showed her friends. “It’s a lingerie photo that I send all my guys. And then he was like, ‘Let me know about New York,’ because he’s gonna be in New York when we’re there, and I was like, ‘Oh yeah, come out with us.’ He goes, ‘Ugh, we should’ve kissed,’ and I go, ‘Yeah, we really should’ve. There’s still time in New York.’”

“He goes, ‘Wait, are you ovulating? Why the change of heart?’” she continued, laughing. “I go, ‘I woke up horny.’ And then he goes, ‘F— my life, catching the next flight back.’ I go, ‘Let’s go!’”

Cavallari, not sure how much of her was serious at that moment, confessed: “This is what I do, though, this is what I do. Then tomorrow I’ll be like, why is Harry hitting on me? Like, I did this.”

Later that day, she received another message from Jowsey, but far more explicit than before.

“Look what he just texted me,” she said, passing her phone around to her friends. “The highs and lows, man. Harry’s f—— hot. I would maybe make out with him in New York.”

Cavallari said she knows what she wants for her future, despite her past flings.

Cavallari was previously married to Jay Cutler, with whom she shares three children. The couple split in 2020 after seven years of marriage, and she has since been linked to comedian Jeff Dye, country singer Chase Rice, NHL player Nate Thompson and her more recent ex-boyfriend, Mark Estes.

“I know that Harry is an absolute player, and I know, I did the young thing, okay?” she later told cameras. “I dated a 24-year-old. Historically, the guys that I’m attracted to are not the types of guys I should be with long-term.”

“Talan [Torriero] wasn’t wrong,” she added of a comment an ex Laguna Beach costar made about her romantic life in recent years. “I mean, since my divorce, I’ve been thinking with my chi chi!”

Honestly Cavallari: The Headline Tour airs Wednesdays at 10 p.m. ET on E! and can be streamed on Peacock.