- Jake Paul’s romantic history includes a fake wedding, a gold medal Olympian, and one of the messiest on-and-off relationships the internet has ever witnessed
- From fellow Team 10 members to world-champion athletes, Paul’s love life has always been as chaotic as his career
- He is currently engaged to Dutch speed skater Jutta Leerdam, who just made history at the 2026 Winter Olympics
If you thought Jake Paul’s boxing career was dramatic, wait until you take a deep dive into his love life. The 29-year-old YouTuber-turned-professional boxer has dated, fake-married, and publicly broken up with some of the most recognizable names on the internet. And every single time, it was loud, messy, and absolutely impossible to look away from. Whether you’ve followed his journey from the very beginning or you only know him as Jutta Leerdam’s fiancé, here is the full, unfiltered story of Jake Paul’s relationship history.
It Started With Alissa Violet and a Whole Lot of Drama
Jake Paul and his fellow Team 10 member Alissa Violet had an on-and-off relationship from 2015 to 2017. Although Alissa claims they were never official, their tumultuous relationship played out in the public eye. And by public, we mean the kind of public that ends with someone uploading a Snapchat of themselves walking out of a house with packed bags.
Alissa uploaded a video on Snapchat with her bags packed, saying that Jake had kicked her out of the Team 10 house, leaving her with nowhere to go. Jake later claimed that Alissa had cheated on him with his brother, Logan. Alissa pushed back hard, claiming in a YouTube video that Jake frequently had other women over in front of her, that he played mind games, and that she would cry herself to sleep every night. It was messy, it was viral, and it was just the beginning.
In 2018’s The Mind of Jake Paul docuseries, Alissa said: “We never officially dated, ever. Which there are so many things out there like ‘Jake Paul’s ex-girlfriend,’ and I’m always the ex. It was just hooking up, and I’ve chased him for so long, and I wanted him to be my boyfriend.” Whether or not there was ever a real relationship, the fallout was very real, and it set the tone for everything that came after.
Erika Costell and the “Jerika” Era
Jake Paul started dating fellow YouTuber Erika Costell early in 2017. In June 2017, Paul posted a YouTube video that appeared to show the couple getting married. They also released a song about their relationship called “Jerika,” which peaked at No. 86 on the Billboard Hot 100 chart.
Yes, they had a charting song. Yes, it was called “Jerika.” Yes, this was real life.
Their relationship started as just for YouTube views in 2017. However, they then developed real feelings for each other and split in November 2018. A few weeks after the breakup, a photo of the two eating lunch together went viral, sending their fans into a full spiral. Jake denied that anything was happening, said it was just two people catching up. Nobody fully believed him, but that was kind of the whole vibe of the Jake Paul era.
The “Fake Wedding” With Tana Mongeau
This is where things truly went off the rails.
One of Jake Paul’s most high-profile relationships was with fellow YouTuber Tana Mongeau. About one month after the pair started making videos together, Paul asked Mongeau to “marry him” while celebrating her twenty-first birthday in Las Vegas. The proposal happened via bottle service, complete with a birthday cake, a giant diamond ring topper, and the words “Will you marry me, Tana?” spelled out in icing. Paul described the relationship as: “It’s real, but it’s also not. But it also is, so it’s weird, man.”
The couple married in a televised wedding at Graffiti Mansion in Las Vegas on July 28 for MTV. However, nearly two weeks after tying the knot, she admitted that she and Paul were not legally married. Then, in January 2020, they announced a break. The break became permanent. The fake marriage became a footnote in internet history.
Julia Rose and the On-and-Off Chaos That Lasted Three Years
Jake Paul and Julia Rose first met on the set of a music video. Rose played his girlfriend in the video, and apparently, the romance blossomed quickly after that. And in what might be the most on-brand Jake Paul moment imaginable, he fell hard and fast. According to a December 2021 interview, it was love at first sight. Paul said, “I told her I loved her the first day that we met. I’ve never done that ever.”
What followed was one of the most exhausting on-and-off relationships the internet has ever had to keep track of. They broke up, they got back together, she proposed to him on Entertainment Tonight, he broke up with her again because she did not post about his NFT project, and then they reconciled, and then split again. They have split up more than four times since they met in 2019.
The final nail in the coffin came in December 2022, when Paul put a telling caption on one of his Instagram posts that simply read “Picked the wrong, Rose.” Then on Valentine’s Day 2023, he posted photos of himself with his boxing gloves and captioned it “Happy Valentine’s Day from me n’ mine. I love you, babe,” making it devastatingly official. Page Six reported at the time that Paul was reportedly devastated by the split, even though he was the one sending the cryptic Instagram messages.
A source also told outlets that in the aftermath, Paul briefly dated model Sky Bri, and the two even got matching tattoos, which Bri later confirmed were done as an act of revenge against Rose. Julia was not pleased, and she made that very clear online.
Jutta Leerdam: The One Who Changed Everything
And then, in a plot twist that nobody saw coming, Jake Paul slid into the Instagram DMs of a Dutch speed skating world champion and somehow ended up with the love of his life.
Jake Paul sent Leerdam a DM on Instagram and asked if she wanted to be on his podcast. “I was like, ‘Okay, let’s do it. Can be good, can be nice,” she recalled. Leerdam had her reservations. She assumed he would be the brash, controversy-loving internet personality the world knew him as. “I never, ever expected to date him, like never,” she admitted.
But something shifted. “We really clicked in these two fast-paced worlds on a deep and super personal level,” Leerdam said. In April 2023, Paul “hard-launched” their relationship on Instagram with the caption, “I’m Dutch now.” The internet immediately lost its mind.
While seemingly on a tropical vacation, Paul proposed to Leerdam on March 21, 2025. The couple announced the news the next day in a joint Instagram post, writing: “We can’t wait to spend forever together.”
And just when you thought the story could not get any more cinematic, on February 10, Paul was visibly emotional as he watched his partner secure gold at the Milan-Cortina Winter Olympics, with Leerdam winning the women’s 1,000m competition. There he was, the same guy who once fake-married a fellow YouTuber for MTV views, crying in the stands at the Winter Olympics while his fiancée broke an Olympic record.
Following her success in Italy, Leerdam was honoured with the title of Knight of the Order of Orange-Nassau, a Dutch civil and military award given to those deemed to have made an impact on society. And Paul, still recovering from a broken jaw he suffered during his December 2025 loss to Anthony Joshua, was right there beside her.
The guy who built his brand on chaos is now planning a wedding with a seven-time world champion Olympian. Jake Paul relationship history is a lot of things, but boring is not one of them.
