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Tennis is usually about the solo grind. One player, one court, nowhere to hide. But when you’re the world number one and you start dating a fellow pro, the spotlight gets blinding. Fast. That’s exactly what happened with Jannik Sinner and Anna Kalinskaya.
The rumors started as a low hum in early 2024. Fans noticed they were practicing at the same clubs. Then came the "Anna" caller ID leak on Jannik’s phone. By the time the French Open rolled around in May 2024, the secret was out. Sinner, usually the most tight-lipped guy on tour, finally caved.
"Yes, I'm with Anna," he told reporters. He followed it up with his classic "but we keep everything confidential" line. Honestly, it was a breath of fresh air to see him happy. But in the world of pro sports, happiness is often as fleeting as a tie-break.
The Rise and Fall of the Tennis Power Couple
For a few months, they were the sport’s golden pair. You’d see Anna in the box during Jannik’s matches, and he’d return the favor, often hiding under a hoodie in the stands to watch her play. The peak of it all was the 2024 US Open. Jannik won the title, and the image of him kissing Anna in the stands went nuclear on social media. It felt like they had figured out the impossible: how to balance two grueling travel schedules and a high-stakes romance.
Then things got quiet. Real quiet.
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By the end of 2024, the digital breadcrumbs started disappearing. Anna unfollowed him on Instagram. She didn't show up at the ATP Finals in Turin. Instead, she was posting vacation photos from Miami while he was battling for Italy in the Davis Cup. In the world of modern celebrity, an unfollow is basically a legal separation.
The May 2025 Bombshell
People kept guessing until May 2025. Jannik was making his big comeback at the Italian Open after a three-month doping ban—a suspension he accepted to avoid a longer legal battle over a contaminated massage cream. The press was hungry. Not just about his fitness, but about his heart.
He didn't dodge the question.
"I was very surprised to see some pictures, which, you know, nothing serious. I'm not in a relationship. So, whoever is asking, that's it."
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Basically, he shut it down. It wasn't a messy breakup, at least not publicly. It was just... over.
Why Jannik Sinner and Anna Kalinskaya Couldn't Make It Work
Honestly, it probably comes down to the math. Professional tennis players are on the road for 40+ weeks a year. They are rarely in the same city at the same time unless it’s a Grand Slam or a combined 1000-level event. Sinner himself admitted to Vanity Fair Italia that juggling a relationship at the top of the game is a massive challenge. He's a guy who obsesses over every detail of his training. When you're chasing Grand Slams, there's very little room for anything else.
There was also that weird tension with Nick Kyrgios. Anna used to date the Australian "bad boy" of tennis, and Kyrgios wasn't exactly quiet about Sinner’s doping case. He took several shots at Jannik on social media. While Sinner is too composed to let that get to him, having your girlfriend's ex-boyfriend constantly trolling you in the press can't be fun for anyone involved.
The Lara Leito Rumors
Right after the split, the Italian tabloids went into overdrive. Chi magazine published photos of Sinner with Lara Leito, a Russian model who previously dated actor Adrien Brody. They were spotted at the Monte Carlo Country Club.
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Is it serious? Jannik says no. During that same Rome press conference, he labeled those photos as "nothing serious." He seems focused on one thing: getting his ranking and his reputation back to where they were before the suspension.
What We Can Learn From the Sinner-Kalinskaya Split
The most interesting thing about this whole saga is how much it humanized Jannik. We see these athletes as robots, especially Sinner with his icy composure on the baseline. But seeing him navigate a very public relationship—and an even more public breakup—reminded everyone that he’s just a guy in his early twenties trying to figure it out.
If you're following this story, here is the reality of the situation right now:
- Relationship Status: Both are officially single as of early 2026.
- Social Media: They no longer follow each other. The era of the "heart" emojis in the comments is over.
- Focus: Sinner is currently prioritizing his post-ban career trajectory, while Kalinskaya is focused on breaking back into the WTA top 20.
The take-away? Don't believe every "engagement" rumor you read on TikTok. Back in late 2024, people were convinced they were getting married because Anna was wearing a ring on her right hand. Pro tip: Russians often wear wedding rings on the right hand, but it turned out it was just a regular piece of jewelry.
If you want to keep up with what's actually happening, watch the player boxes during the next Major. In tennis, the guest list in the box tells a much truer story than a press release ever will. For now, the box is reserved for coaches and family. Jannik is back to flying solo.