Inside Harry Jowsey's Dating History Full Of Hollywood Hotties

The man, the myth, the legend; Harry Jowsey certainly has a star-studded dating history, and there's no sign of slowing down. The Australian-born bachelor first appeared on a New Zealand reality dating show, "Heartbreak Island," before gaining notoriety in the States on the first season of "Too Hot to Handle" in 2020.

Since the show's release at the dawn of the COVID-19 pandemic, Jowsey quickly became a household name, as did the roster of beautiful women he has dated. Since his stint on "THTH," Jowsey went on to appear on other dating shows like "Match Me If You Can" and "Perfect Match." He's also attempted to dip his toe into the controversial world of non-romantic reality shows, like "Floor is Lava" and "Dancing With the Stars." (though, we're not sure if he knew that wasn't a dating show).

Now a self-proclaimed dating expert, Jowsey has turned to content creation to provide his two cents with the podcast "Boyfriend Material." How exactly did he become the all-knowing master of relationships? We're here to give you a look into Harry Jowsey's dating history to find out.

Harry Jowsey almost had it all when he left Season 1 of "Too Hot to Handle" in a steamy relationship with influencer Francesca Farago, even after almost losing their co-stars thousands of dollars. The concept of the reality dating show is to put attractive, eligible singles in close quarters, except every time they romantically touch a member of the opposite sex, they lose varying amounts amount of money for the entire cast. During the first season, Farago and Jowsey famously almost lost $30,000 due to their inability to keep their hands off of each other, but they managed to restore the cash that they lost and ended the season still in a couple.

Unfortunately, life outside of the "THTH" villa wasn't all it was chalked up to be. Since Jowsey is from Australia and Farago is originally from Canada, traveling to see each other put a bit of a strain on the relationship. They broke up for a few months between 2019 and 2020 (the season was filmed pre-pandemic in 2019), but time would prove, once again, that they couldn't keep their hands off of each other. They got back together when the season aired, complete with a ring-pop engagement during the Zoom reunion special (Farago later admitted to Variety that the nature of the proposal was satirical and they weren't engaged). 

Come June  2020, they both would post videos to YouTube detailing their breakup, insinuating that it was Jowsey who did the dumping this time around. "I just had to end it because ... I knew that if I continued to be with Francesca that it would end up with her being seriously heartbroken or me continually being seriously depressed in the relationship," he said in the now-deleted video.

Harry Jowsey couldn't hold back his fury when his then-girlfriend Julia Rose supposedly backslid with her ex, Jake Paul. Jowsey and Rose began seeing each other during his first break-up with Francesca Farago, and while she and Jake Paul were on a break. Seems like a match made in heaven if you ask us.

It didn't take long for the couple to endure some trouble in paradise. It was the classic case of he-said-she-said when Jowsey went on the "BFFs" podcast with Josh Richard, Brianna LaPaglia, and Dave Portnoy, to air out all of Rose's dirty laundry. He said the two dated for about a month back in October 2020 when she cheated on him in Vegas with Paul.

After all of this supposedly went down, The Hollywood Fix asked the influencer if he had seen that Rose and Paul had been posting together on social media. "Sh*t is crazy. That's how I found out she [was] cheating on me. If she had to use me to get back with someone that she is happy around then that's fine." Rose recounted the events a little differently as she went on Jake's brother Logan Paul's podcast "Impaulsive," and remembered that he was probably more into the relationship than she was. "He was very wanting love ... and I felt like you know those people that if they're looking for a relationship through anything it was like they'll take any kind of relationship that they can get. It was super super fast and a lot of different red flags came up," she continued, "I kind of said I felt he was dating me for the wrong reasons."

Harry Jowsey couldn't get enough of his fellow "Too Hot to Handle" alums. When he and Francesca Farago called it quits for the final time in 2021 Georgia Hassarati, another contestant from the first season "Perfect Match," and the third of "Too Hot to Handle," caught his eye. The two Aussie natives immediately connected and began dating in June 2022, but the short-lived relationship headed south quickly. 

He went on the "Call Her Daddy" podcast in July 2023 and made some wild claims about an unnamed woman that viewers were insisting was Hassarati. "I think when they start to take a fancy for other guys while you're in a relationship, that tends to like... that will really set you over that line. You have a boyfriend—you shouldn't be, like, bouncing on that guy," expressed Jowsey during the interview. Hassarati wouldn't let him get away with the claims without defending herself, as she turned to TikTok to retaliate. "I let him do what he did and break up with me with a pathetic handwritten letter that he left on his bed ... I didn't look back. Now, he's so angry that I wasn't trying to get back with him or trying to kiss his a**, so he has to publicly degrade me further, like it wasn't enough during our relationship."

Beyond Hassarati, Jowsey was linked with Jessica Vestal from "Perfect Match" season 2. They were coupled up for the entirety of their season and continued to date for another month and a half after its wrap in 2023 when Jowsey was supposedly getting too cozy with yet another costar, Melinda Melrose. During a joint interview with Entertainment Tonight in June 2024, the two remarked that they were grateful for their time together, so at least there's a silver lining in there somewhere.

Harry Jowsey made a stop at the ballroom in 2023 during his reality television world tour, and once again sparked up dating rumors with one of the leading ladies. "Dancing With the Stars" territory comes with showmances that are often played up to draw in viewers, so rumors like this are to be expected for anyone that graces the dance floor.

The speculation began outside the studio, as there were more and more instances of Jowsey and Arnold spending time together outside rehearsals. They were seen holding hands at the Hollywood Palladium in October 2023. Then, like a domino effect, they were eliminated during week 9 in November 2023. Thanksgiving fell on the same week, he posted a Snapchat story gifting her a Van Cleef bracelet that's estimated to cost a whopping $14,500 as a token of his appreciation. Then, the Aussie crashed Arnold's beachfront Thanksgiving plans, and Arnold made it known by posting a now-deleted photo to Instagram of her hand on Jowsey's chest and his around her waist.

Those thoughtful gestures and gifts are surely the doings of two people in a committed relationship, right? Nope, there's confirmation that the two were never romantically intertwined. During an episode of his podcast "Boyfriend Material" in April 2024, Jowsey exclaimed: "I'm sorry if this answer breaks some hearts, but I'm here to confirm once and for all, Rylee and I have never been [in] any type of relationship. We never leaned into it. We never were putting on an act or anything like that. It was just organic. What you saw is kind of how it was. That was just amazing love and amazing friendship, and just an amazing bond that we had together." What a shame, we were really rooting for this one!

Love hasn't always been kind to Harry Jowsey, his solution? Shooting his shot with other celebs. You never know, it could work (spoiler alert: it didn't).

Back in 2022, some rumors were circulating the internet that Jowsey and Khloé Kardashian were an item. While there was never any truth to that, Jowsey revealed on his "Tap In" podcast that he had attempted to reach out to her in the months prior. "The thing is, I DM'ed her a couple weeks before and was like, 'How are you little hummingbird?' ... because I was like, I wonder if I just cast a line here," he admitted, after revealing that the two were never truly an item.

During an episode of the "Let's Be Honest" podcast with Kristin Cavallari in January 2025, Jowsey revealed that he threw his hat in the ring with Sabrina Carpenter when she and Barry Keoghan had supposedly called it quits, but there weren't fireworks, in the sense that she never responded. As it stands, Jowsey announced that he's celibate as of late to Cavallari, and is working on himself before he welcomes another woman into his life. "My dad died, and I was like, 'I'm not horny,'" he explained. "Then I was like, 'I'm not talking to anyone, so I'm just gonna lay off it for a bit' ... I'm not really there yet, so I really need to do the groundwork to get myself more presentable, more attractive and, I guess, more locked in on who I want to become."