A Complete Timeline of 'Let's Marry Harry' Star Harry Jowsey's Complicated Dating History

Harry Jowsey’s name might conjure up the words “playboy” and “heartthrob.” His relationships on Too Hot to Handle and Perfect Match have stirred up a lot of online discussion, but the Australian reality star is now on a mission to change that. His new Netflix reality dating series Let’s Marry Harry is all about him settling down and finding a wife.

Helping Jowsey find true love in an elimination-style competition series are his best friends Sonny Henty and Amanda Kloots, as well as his Perfect Match ex-girlfriend Georgia Hassarati. That last name might raise some eyebrows, as Jowsey and Hassarati broke up amid rumors of infidelity—but Jowsey told US Magazine that Hassarati showed up for him in a time of need, which helped mend their relationship. “When my dad had passed, she was one of the handful of people who reached out,” he told the publication. “And when we sat down again after all these years, we laughed about all the things [that happened].”

Though the reality star insists he’s ready for something serious, Jowsey is best known for his loaded—and public—dating history. For anyone who hasn't kept up with Jowsey’s influencer lore and love life, read on for a primer on his dating timeline and what to expect in his Bachelor-esque foray to find a wife.

Harry Jowsey's Complete Dating History

Harry Jowsey was engaged to Francesca Farago

Jowsey and Francesca Farago's on-again-off-again relationship began when they both starred in Too Hot to Handle, coupled up, and established themselves as the rule-breakers who spent several thousand dollars on activities that the robot host, Lana, did not approve of. The pair were still together when they left the show, and they even visited each other in their respective countries—Farago traveled to his home in Australia, and Jowsey flew to hers in Canada—but the pair eventually broke up by the summer of 2019.

However, by the time THTH season 1 dropped on Netflix in April 2020, the couple were back together, despite staying in different places during the pandemic. (Harry was in L.A. by then, while Francesca was still in Canada.) They even got engaged—with a Ring Pop proposal—during the Zoom reunion for Too Hot to Handle. Alas, the pair wasn't meant to be. In June 2020, per PEOPLE, the two released separate YouTube videos about their breakup, in which they revealed that Jowsey had ended things due to issues including long-distance.

Harry Jowsey was linked to 'Too Hot to Handle' costar Madison Wyborny

Following his breakup with Farago, Daily Mail Australia linked him to his former Too Hot To Handle costar Madison Wyborny in May 2020. However, Jowsey denied the rumor, stating that the two had hooked up but not dated during his 2019 break with Farago. “We hooked up a couple of times, and then things ended with that quite quickly because she was, like, testing me,” he said during an appearance on the “Watch With US” podcast. "I wouldn't text her for a couple of days, and then she's like, ‘Oh, you almost failed that test.’”

After Jowsey and Farago rekindled their romance, Wyborny told Elite Daily that her and Jowsey’s relationship had been real, while his recoupling with Farago was a PR stunt. Wyborny claimed that she and Jowsey were still dating in February 2020 when he supposedly got back together with his ex, claiming she found out from a friend’s Instagram Story. “He could have told me, 'Hey, I'm not really feeling this anymore. I'm going to get back with Francesca,'" Madison said at the time. “It just hurts so bad to know someone you were basically in a full-on relationship with could say such hurtful things about you, just for publicity.”

Harry Jowsey was linked to Kylie Jenner's BFF, Stassie Karanikolaou

Since he moved to L.A. following his Too Hot to Handle season, Jowsey has been linked to several reality stars and influencers, including Wyborny, YouTuber Charly Jordan, influencer Julia Rose, influencer Mia Francis, and podcaster/YouTuber Tana Mongeau. One of his most high-profile dating rumors was with YouTuber Anastasia “Stassie” Karanikolaou, who's been besties with Kylie Jenner since middle school and is also close to the rest of the Kardashians, Kendall Jenner, and Hailey Bieber.

According to E! News Online, rumors swirled after Karanikolaou made some appearances on Jowsey's social media. However, the pair never commented directly on the relationship, and according to Nicki Swift, some fans were skeptical about whether they were ever serious.

Harry Jowsey has slid into Khloé Kardashian's DMs

In February 2022, rumors began swirling that Jowsey and Khloé Kardashian were "talking," according to PEOPLE. During an episode of his podcast “Tap In” released that month, Jowsey confirmed the speculation wasn't true, but admitted that he had slid into her DMs a couple of weeks earlier.

"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 said on his podcast. "I'm tall. I kind of look like a basketball player, maybe. I'm just unathletic...She's going through a tough time. Maybe she needs a laugh. Maybe she needs someone who's just going to come and make her giggle and have a good time."

"And then all this shit comes out," Jowsey added, referring to the January 2022 reveal that Kardashian had broken up with her ex Tristan Thompson. "She probably thinks I'm a piece of shit."

As for Kardashian, she responded to the rumors before Jowsey did. Per PEOPLE, she replied directly to a fan page that shared the rumors, writing, "ABSOLUTELY NOT TRUE."

Harry Jowsey dated Georgia Hassarati after 'Perfect Match' season 1

Like many reality shows, Perfect Match season 1 continued generating drama even after the cameras stopped filming. In season 1, Too Hot to Handle alum Georgia Hassarati and The Mole star Dom Gabriel were chosen as the strongest couple on the show and won a weeklong vacation anywhere in the world. However, the pair faced difficulties in their relationship after Perfect Match finished filming in early 2022. (Hassarati and Gabriel have different accounts of how long they stayed together.)

A few months after Perfect Match ended, Jowsey and Hassarati met when she appeared on his podcast “Tap In.” They soon began dating, though they claim different timelines of when; Jowsey has said they hooked up the same night they met, while Hassarati denies the claim. Regardless, the two Aussies soon made their relationship official, and they dated on and off for about a year until April 2023, per E! News. They both accused the other party of cheating during their relationship, but patched things up after Jowsey’s father passed away, which led to Hassarati joining Let’s Marry Harry.

Harry Jowsey had a "secret girlfriend" while he was on 'Dancing With the Stars'

In fall 2023, Jowsey joined one of the longest-running reality shows ever, competing on season 32 of Dancing With the Stars. Rumors about his dating life soon followed, with fans theorizing that the then-27-year-old influencer was secretly dating his DWTS partner, 18-year-old professional dancer Rylee Arnold—especially since DWTS has a history of relationships among its cast.

However, the dance partners made it clear throughout their season that despite their chemistry, they were not in a romantic relationship. Speaking with PEOPLE, Jowsey said of the rumors, “I think that it's a little bit unfair on Rylee so early on. She's so green to this whole world and everyone having an opinion, and stuff like that...We're trying our best to focus on the dance, and whatever happens, happens. We’re just enjoying being together.”

However, it turned out that Jowsey was privately seeing someone during his DWTS tenure. In the first episode of his podcast “Boyfriend Material” (produced by Unwell, the network from “Call Her Daddy” star Alex Cooper), the host revealed that he was in a relationship he kept private while on the show. "What if told you I was actually in a secret relationship at the start of Dancing With the Stars? All those edits and all that stuff kind of brought me and my girlfriend at the time apart,” he said.

He didn't reveal any details and bleeped out his mysterious ex’s name, though he did tell her, 'I miss you.' There have been no clues since, and Jowsey later mentioned that the relationship fizzled. “It's so difficult to see your boyfriend or girlfriend on Dancing With the Stars being that close with someone else,” he explained on an episode of his podcast.

Harry Jowsey paired up with Jessica Vestal on 'Perfect Match'

Jowsey debuted on Perfect Match season 2 in the premiere episode and initially paired up with fellow cast member and former Too Hot to Handle winner Elys Hutchinson. However, after the pair didn't work out, Jowsey matched with Love Is Blind alum Jessica Vestal. He and Vestal remained coupled over the show's first six episodes—making them one of the longest-lasting couples in the house. Jowsey even opened up about how much he admires Vestal, frequently praising her in confessionals for being a loving single mother and his physical type.

However, the two had to contend with Jowsey's reputation in the Netflix reality sphere. Many of the women on the show commented on how Jowsey may not be trustworthy, and even Dom Gabriel, who is now close friends with Jowsey, noted Harry's questionable behavior. Gabriel's comment led to an argument between Vestal and Jowsey, and though he claimed that he's turned over a new leaf—he was supposedly in his therapy era during the show—and he's serious about her, Jowsey later admitted on his podcast that he kissed fellow contestant Melinda Berry behind Vestal’s back. Jowsey and Vestal broke up a month after filming ended.

Harry Jowsey was linked to two public figures in 2025: Lucy Hale and Sia

After his Perfect Match relationship fizzled, Jowsey was briefly linked to actress Lucy Hale in March 2025. Per PEOPLE, the relationship was “super casual but not brand new.” An US Weekly source added that Jowsey “initiated things” by (yet again) sliding into her DMs, and they hit it off by bonding over their mutual sobriety. “It’s casual, and they are having fun, but Harry is very into Lucy,” the source continued. “Friends around them think they are very cute and are a good, yet surprising match.” Neither Jowsey nor Hale ever publicly acknowledged the rumored romance, so we’ll never know exactly how long they were together or what drove their breakup.

Not long after that rumor, Jowsey was spotted holding hands with singer-songwriter Sia in July 2025. Their age difference and Sia’s recent divorce sparked some skepticism, and Sia later promoted Let’s Marry Harry, calling him “a dream” while simultaneously rendering this link-up a likely PR relationship and nothing more.