The tennis world is no stranger to Nick Kyrgios’s flair for stirring the pot, but his latest comment—a succinct four-word reaction to his ex-girlfriend Anna Kalinskaya’s quarterfinal run at the 2025 Citi DC Open in Washington, DC—has sparked intrigue without the usual controversy. On July 23, 2025, the Australian tennis star, sidelined by injury but ever-present in the sport’s narrative, took to social media to acknowledge Kalinskaya’s achievement, writing, “Proud of you Anna.” The understated message, a departure from his typically provocative style, comes months after Kalinskaya’s high-profile split from world number one Jannik Sinner and follows a year of personal and professional turbulence for both players. As Kalinskaya shines on the WTA Tour, Kyrgios’s gesture has reignited discussions about their past and his evolving public persona.
Kalinskaya, the 26-year-old Russian ranked world number 12, has been a standout in 2025, with her Citi DC Open quarterfinal run marking another milestone in a breakout season. Her journey to the last eight included a commanding 6-4, 6-3 victory over Ons Jabeur, showcasing the aggressive baseline game that propelled her to a career-best ranking and a Dubai WTA 1000 final earlier this year. “I’m just enjoying playing tennis and competing at this level,” Kalinskaya said post-match, her focus evident after overcoming a wrist injury that forced her to retire at Wimbledon. Her success in Washington DC, a key US Open warm-up event, positions her as a dark horse for the upcoming Grand Slam, where she reached the third round in 2024.
Kyrgios’s reaction is notable given their complex history. The pair dated briefly in 2020, a relationship that ended on strained terms, with Kalinskaya reportedly calling Kyrgios a “bad person” during an Instagram Live session, though she later clarified the comment wasn’t about him. “We broke up. We aren’t friends,” she said at the time, while Kyrgios downplayed the split, noting, “Nothing happened. We just went our separate ways. Unfortunately things didn’t work out. We had some fun memories.” Their past resurfaced in 2024 when Kyrgios sparked outrage with a now-deleted “second serve” comment on a photo of them together, widely interpreted as a misogynistic jab at Kalinskaya’s then-relationship with Sinner. “I’m the one that’s the bad guy for saying something about it? I never brought it up lol,” Kyrgios defended himself, but the backlash led to calls for ESPN to remove him from his US Open commentary role.
The Sinner-Kalinskaya romance, confirmed in May 2024, ended in May 2025 after Sinner’s three-month doping suspension, a saga that Kyrgios vocally criticized, calling the verdict a “sad day for tennis.” Sinner, addressing his split at the Italian Open, said, “I’m not in a relationship. So, whoever is asking, that’s it. It’s all good.” Kalinskaya’s focus remained on her game, with her Citi DC Open performance proving her resilience. “She also had an amazing week,” Sinner had said of her Berlin run in 2024, a sentiment that echoes her current form.
Kyrgios, now 30 and dating Australian influencer Costeen Hatzi, has been limited to just one ATP Tour match in 2025 due to ongoing wrist and knee injuries. His commentary stints, including for ESPN, have kept him in the spotlight, though his outspoken nature—evident in his doping critiques of Sinner and Iga Swiatek—continues to polarize fans. Yet, his recent praise for Kalinskaya, shared via Instagram Stories, suggests a softer side. “Amazing tennis player and also part of the @thisisevolve team!!” he wrote earlier in 2025, referencing their shared management under Naomi Osaka’s Evolve agency. This latest comment, “Proud of you Anna,” marks a rare moment of diplomacy for the self-styled “bad boy of tennis.”
The tennis world has taken note of Kyrgios’s shift. Once criticized for comments like his 2015 sledge to Stan Wawrinka—“Kokkinakis banged your girlfriend”—he appears to be navigating a path toward maturity, perhaps influenced by his own career uncertainties. Kalinskaya’s rise, meanwhile, underscores her growing stature. With over $3 million in career earnings and a 2024 Australian Open quarterfinal to her name, she’s no longer defined by her past with Kyrgios or Sinner. As the US Open looms, her Citi DC Open run signals a player peaking at the right time, while Kyrgios’s words hint at a newfound respect, closing a chapter of tension with a gesture of goodwill.
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