Few public figures have blurred the line between entertainment and reality quite like Jake Paul, and his romantic history is a reflection of that duality.
From headline-grabbing YouTube “marriages” to his current, more grounded relationship with world champion speed-skater Jutta Leerdam, Paul‘s love life charts his evolution from digital disruptor to disciplined athlete.
What began as a string of content-driven romances has gradually transformed into something more authentic, mirroring the boxer’s own shift toward credibility and maturity beyond the screen.
A 2019 Las Vegas spectacle
Paul began dating the YouTuber Tana Mongeau in April 2019, and by June of that year, Paul appeared to propose to her on her 21st birthday.
In July 2019, Paul and Mongeau held an over-the-top Las Vegas “wedding,” complete with a private jet, cash-splurge staging and a pay-per-view stream.
However, it soon emerged that they had not obtained a marriage license and the officiant lacked proper legal credentials. According to Mongeau:
“To everybody that’s calling it fake because we rushed into it … because I wanted to not do it legally.”
She added, “I think that legally binding yourself to someone takes away the love.”
While the ceremony drew massive online attention, many viewed it more as content than a genuine marriage. The couple ultimately broke up in early 2020.
Mongeau herself said the ceremony was “fun and lighthearted … obviously doing for fun and for content.” Within less than a year, the relationship had collapsed.
Jake later told Entertainment Tonight that, “We all do things sometimes… And sometimes you end up getting fake married. So I’ll leave it at that.”
Engagement to Olympian Jutta Leerdam
In 2023, Paul began a public relationship with Jutta Leerdam, the Dutch Olympian. Their pairing became official in April 2023. Then, on March 22, 2025, the announcement came:
“We’re engaged,” Paul wrote on Instagram. “We can’t wait to spend forever together.”
The images captured show Paul clad in white on one knee, presenting a substantial oval-cut diamond ring while Leerdam, matching in silk, reacts with joyful surprise.
Leerdam later described Paul as: “The most romantic guy in the world. I’m super lucky.”
The Olympic silver medalist in the women’s 1000 m race competed in Beijing 2022 and was already making waves in her sport.
For Paul, whose boxing career has aggressively sought legitimacy, partnering with a serious athlete signaled a shift.
As one source reported, he called her “one of the purest-hearted human beings that I have met in my life”.
Their relationship publicly began when they shared images on Instagram in April 2023; however, it appears their connection started earlier after they initially met via the boxer’s podcast invitation.
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