A Complete Timeline of 'Perfect Match' Star Harry Jowsey's Complicated Dating History

For Perfect Match season 2, Netflix brings back one of the original members of the streaming giant's unscripted universe. Harry Jowsey comes into the forefront on the second season of the streamer's must-watch reality show, which returned on June 7. Jowsey first came to reality TV fame after starring in the first-ever season of Too Hot to Handle in April 2020, where his relationship with Francesca Farago was the main subject of discussion. (If you recall, Farago was a part of the Perfect Match season 1 cast.) Four years later, Jowsey has spun out his reality fame to a stint on Dancing With the Stars, a high-profile podcast, Boyfriend Material, an infamous OnlyFans, and a candle line.

Of course, Jowsey's best known for his loaded dating history, which immediately becomes a contentious subject once he arrives in the Perfect Match villa. For anyone who hasn't kept up with four years of influencer lore, read on for a primer on Jowsey's dating timeline, and how he entered into a love triangle with the winners of Perfect Match season 1.

Harry Jowsey was engaged to Francesca Farago.

Jowsey and 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 robot host Lana did not approve. 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 the long distance.

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 his THTH co-star Madison 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.

Per E! News Online, rumors swirled after Karanikolaou made some appearances on Jowsey's social media. However, the pair never directly commented, and according to Nicki Swift, some fans were skeptical if 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 that was released that month, Jowsey confirmed that 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 at the time. "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 s--- 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 s---."

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, winning 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 offered differing statements on 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 have different claims about when; Jowsey has said that they hooked up the same night they met, while Hassarati denied 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.

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 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 did not have 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 did turn 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's Alex Cooper), the host revealed that he was in a relationship that 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, but assuming that Perfect Match was filmed before DWTS, there is a chance that his clandestine romance could have begun on the Netflix show.

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 have remained coupled over the show's first six episodes—making them one of the longest-lasting couples in the house. Jowsey even opens 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 have already had to contend with Jowsey's reputation in the Netflix reality sphere. Many of the women on the show have commented on how Jowsey may not be trustworthy as a committed partner and even Dom Gabriel, who is now close friends with Jowsey, commented on Harry's questionable behavior. Gabriel's comment led to an argument between Vestal and Jowsey, but he claims that he's turned over a new leaf—apparently, he's in his therapy era—and he's serious about her. Only time (and the remaining Perfect Match episodes) will tell.