Harry Jowsey Lives Up to His 'Bad Boy' Rep with Pic Sent to Kristen Cavallari

Kristin Cavallari's new E! Entertainment reality show "Honestly Cavallari: The Headline Tour" plans on candidly dishing all facets of her life, and the "official supertease" trailer ahead of its June 5 premiere lived up to that promise.

The docuseries follows Cavallari as she brings her podcast "Let's Be Honest" to stages across the country. Each episode features candid conversations with celebrity guests, friends, and fans, diving into topics like relationships, pop culture, and personal stories. Aussie celebrity Harry Jowsey appeared on a January podcast in which he flirted with Cavallari. That led to speculation the two were in a romantic relationship. They later insisted they were just friends; but in a later podcast (seen in trailer), Cavallari tells her audience: "I got a dick pic from Harry, you guys," reports Parade Magazine.

When she showed the pic to her bff and longtime hairstylist Justin Anderson, he said, "It's gigantic!"

Page Six says Jowsey was embarrassed by Cavallari's admission, thumping his head with a microphone.

But it shouldn't be forgotten that the 27-year-old Jowsey became famous in 2020 on the reality series "Too Hot To Handle" when he described his penis as a "boyfriend dick," adding, "it's not too big, it's not too small. Just perfect. Looks pretty."

Jowsey first came to the public's attention when he won the dating show "Heartbreak Island Australia" in 2018. He then came to the United States, where he was cast on "Too Hot To Handle." His sexy, boyish looks and playful manner made him an overnight star. That show's premise brought together a group of sexy singles whose challenge was to remain celibate to win a grand prize of $100,000. Harry's relationship with contestant Francesca Farago made them famous, but also their rules infractions (such as PDAs) led to deductions from the prize money and tension within the contestants. The couple became engaged post-show, but broke up soon after.

Jowsey's celebrity grew as he began modeling and collaborated with such fashion brands as Tommy Hilfiger and Calvin Klein. He went on to launch a clothing brand called Naughty Possums, and co-owns Kensington Sunglasses. He also hosts the podcast "Boyfriend Material with Harry Jowsey," and has appeared on other shows like "Dancing with the Stars" and the second season of "Perfect Match."

After his breakup with Farago (done on YouTube), Jowsey has played the field, dating several reality stars, influencers, and models, including another "Too Hot To Handle" cast member, Georgia Hassarati, with whom he broke up after accusing her of cheating. The Cut reports Jowsey "was rumored to have flings with longtime Kardashian hanger-on Stassie Karanikolaou and OG YouTube star Tana Mongeau.

"In 2022, a Kardashian fan account posted a rumor that Khloé Kardashian was 'DM-ing back and forth' with Jowsey," The Cut went on to add, "but Kardashian denied the story herself in the comments. 'ABSOLUTELY NOT TRUE,' she wrote. Phew."

When he appeared on "Dancing With The Stars" last year, it was rumored he was dating his partner Rylee Arnold (who was just 18 at the time). But on the premiere episode of his podcast, he shot the rumor down, saying they were just friends and (at the time) he was dating someone else. "But remember, guys: I had a secret girlfriend at the time, so I wasn't even thinking about that. I was on my good-boy behavior," he said. But he didn't reveal the identity of the "secret girlfriend," because they had broken up.

The girlfriend, though, later revealed herself to be his "Perfect Match" co-star Jessica Vestal, who Jowsey was with for a month and a half just prior to his "Dancing" appearance. At first, she supported his flirty relationship with Arnold, |reported People Magazine. "However, Vestal said the 'last straw' was when Jowsey vowed to 'lighten the load' concerning how much he and Arnold teased their chemistry on social media.

" 'I was understanding of our relationship having to be a secret for a while, but it's kind of excruciating watching the world think you're in love with someone else,' she continued. 'I was just like, I can't do this anymore. I'm not doing this. And we broke up the next day and didn't talk.'"

Last month the tabloids and social media were abuzz about Jowsey's latest relationship with "Pretty Little Liar" actress Lucy Hale. A source told People Magazine that the relationship is "super casual, but not brand-new."

"According to Deuxmoi, the two had a dinner date at the celeb-friendly Corner Store in New York last week. Us Weekly reports that Jowsey 'initiated things' with Hale by sliding into her Instagram DMs, and that they bonded over their mutual sobriety (Hale has been sober since 2022, and Jowsey announced his desire to get sober at the beginning of this year)," reports The Cut.

Check out these pics from Jowsey's Instagram: