Over the years, podcaster and media personality Harry Jowsey has pretty much earned a reputation for being reality TV’s top womanizer. He’s appeared on shows like Too Hot to Handle, Dancing With the Stars, and Perfect Match, and now, he’s seriously searching for his future wife on Netflix’s latest series, Let’s Marry Harry.
When he initially dropped the news on 7 July, Harry called up a bunch of his famous friends, from The Secret Lives of Mormon Wives’ Jessi Draper and Taylor Frankie Paul, his rumoured fling (???) Sia, and his potential wedding singer/fellow Aussie, Cody Simpson. Needless to say, they were all pretty shocked that Harry was throwing a whole wedding without one major component: a wife.
That being said! Now seems like a good time to brush up on Harry Jowsey’s dating history before we meet all the girls vying for his heart on Let’s Marry Harry.
2018: Georgia Byers
Believe it or not, Too Hot to Handle wasn’t Harry’s first foray into reality TV. He met Georgia Byers on the New Zealand dating show Heartbreak Island in 2018, where they eventually won and split the $100,000 prize. However, they ended up breaking it off six months after filming ended. Womp.
Per Harry (via The Sun): “Georgia didn’t appreciate girls commenting on my Instagram pics. We drifted apart.”
2019: Francesca Farago
Though it didn’t premiere until 2020, the first season of Too Hot to Handle was filmed in April 2019, which is where Harry connected with fellow hottie Francesca Farago. After filming wrapped, the two went on to date for a few months before splitting sometime in July 2019.
“I think we had a few miscommunication areas, and we just didn't see eye to eye on a couple of things,” Harry later explained to Glamour. “Plus, I was in Australia and New Zealand at the time. I was just packing up my life to get ready to do the big move. So it was a massively stressful time, and I think I dumped a lot of my stress and pressure on Francesca.”
2019–2020: Madison Wyborny
After Frarry ended (the first time), Harry had an off-camera romance with another THTH cast member, Madison Wyborny, which (according to the Daily Mail) lasted “for months.” Harry confirmed the relationship himself, telling the Daily Telegraph that they “hooked up a couple of times” but “were never anything more than friends with benefits.”
However! Madison later spoke to Elite Daily, claiming that she and Harry had a “real relationship” that lasted up until Too Hot to Handle season 1’s premiere approached and Harry got back together with his onscreen match. Which leads us to…
2020: Francesca Farago (again!)
By the April 2020 premiere of THTH season 1, Harry and Francesca were back on. A month later, Harry even popped the question with a Ring Pop during the THTH virtual reunion special, which was...a choice!
But by June 2020, Francesca revealed in a YouTube video that Harry broke up with her because he no longer wanted to date long distance. Moving on!
2020: Julia Rose
Following his second split from Francesca, Harry had a quick summer romance with Jake Paul’s ex, influencer and model Julia Rose.
During an appearance on the BFFs podcast in April 2021, Harry said it was “a messy situation,” adding, “We were together like every single day for like a month.” According to him, things ended when she cheated on him with Jake (though she told a very different story on Logan Paul’s Impaulsive podcast, where she claimed that her romance with Harry only lasted “a week”).
2022–2023: Georgia Hassarati
Nearly two years passed before Harry connected with fellow Too Hot to Handle alum Georgia Hassarati, who appeared on season three of the show. In June 2022, she served as a guest on Harry’s Tap In podcast, and they hit it off from there. However, by December 2022, Harry claimed to E! News that he was once again single, having split from Georgia back in the fall.
That wasn’t the end of these two, though! They got back together the following year and made several public appearances together before calling it quits (again) in April 2023. Harry later made cheating allegations against Georgia, which she denied, but considering she plays a major role on Let’s Marry Harry, I’d say they’re on good terms now.
2023: Jessica Vestal
Harry made his way back to reality TV with a stint on Netflix’s second season of Perfect Match, where he hit it off with Love Is Blind alum Jess Vestal. Their relationship hit a snag after Harry confessed to kissing their costar Melinda Melrose behind Jess’s back, but the two found their way back to each other after filming wrapped in September 2023.
But then! Harry joined DWTS, and by October 2023, his relationship with Jess was over. The reason? We’ll get to that in a sec.
Without naming names (since Perfect Match season didn’t premiere until that June), Harry later admitted to being in love with Jess during an April 2024 episode of his Boyfriend Material podcast. “I was madly in love with this girl,” Harry said. “It ended up ending, and it fizzled out because it’s so difficult to see your boyfriend or girlfriend on Dancing With the Stars being that close with someone else.” Which brings us to...
2023: Rylee Arnold
At this point, it’s a rite of passage to have dating rumours with your partner on Dancing With the Stars. Naturally, Harry wasn’t immune to the rumour mill when he was paired with Rylee Arnold on the show’s 32nd season. They repeatedly denied that they were anything more than friends, though they had undeniable chemistry on the dance floor.
“Whenever I look at Rylee, I know it’s a safe space, and I know that whatever’s going on outside doesn’t matter. It’s just us there,” Harry told People at the time. They were also spotted holding hands at a Tate McRae concert, further fuelling dating rumours.
To commemorate their time on the show, he reportedly gifted Rylee with a $14,000 18K yellow gold and diamond Van Cleef & Arpels bracelet and even spent Thanksgiving with her and her family.
This was merely a rumour, but if that’s how this man treats someone he’s only friends with…I’m dying to know what being his girlfriend entails.
2025: Lucy Hale
This one’s short and sweet. In March 2025, a People source confirmed that Harry and the Pretty Little Liars alum were an item, saying that it’s “super casual, but it’s not brand new.”
At the time, a separate source told Us Weekly that Harry “initiated things” with Lucy by sliding into her DMs, later adding that they “hit it off” because of their mutual sobriety. “It’s casual and they are having fun, but Harry is very into Lucy,” they shared. “Friends around them think they are very cute and are a good, yet surprising match.”
Their connection seemed to eventually fizzle out, though they never publicly confirmed their romance.
2025: Sia
Harry and Sia first sparked dating rumours in July 2025, when they were spotted holding hands while leaving Ca’ Del Sole in L.A. Of course, fans raised eyebrows as the “Elastic Heart” singer was freshly divorced and nearly 20 years Harry’s senior.
She then called Harry a “dream” and said she’d be applying for Let’s Marry Harry, sooo it’s pretty much giving publicity stunt.
In July 2026, she appeared in his celeb-stacked Let’s Marry Harry promo and jokingly asked whether she was the bride in his wedding. Maybe this was just a rumour, after all!
Let's Marry Harry is now available on Netflix
