Lolita Osmanova, who runs an Instagram diary of her decadent life in Monaco under the name Lola Queen, caused headlines when she hired the Los Angeles theatre where the Oscars ceremony is held for her wedding in 2017.
The daughter of Russian billionaire Eldar Osmanov married Gaspard Avdolyan, whose own father is thought to be worth around $800 million, in a lavish ceremony that reportedly cost $10 million and featured a performance by pop superstar Lady Gaga.
Osmanova and Avdolyan divorced the following year, and she has now posed with Dimitrov after being spotted by eagle-eyed supporters in his guest box at the Vienna Open last week.
The courtship is world number 19 Dimitrov’s third high-profile relationship since 2012, starting when he spent three years with Russian former world number one Maria Sharapova from 2012.
He is likely to have met Osmanova in Monaco, where he has his training base and was reportedly fined by police for speeding alongside Russian ATP finals winner Daniil Medvedev in August.
After splitting from Sharapova, Dimitrov dated former Pussycat Dolls singer and TV star Nicole Scherzinger for around four years before she appeared to cryptically signal the end of their time together on social media last year.
Devoted fans showed their detective skills as they took screenshots of a photo posted by Dimitrov on Instagram Stories and found details about Osmanova on a tennis results site, appearing to show that she was 27 and had played high-level tournaments as a teenager, including junior competitions in Florida between 2006 and 2009.
“She seems like the type he would totally settle down with,” gushed one, while another said: “They look so cute together.”
Dimitrov remained tight-lipped when a reporter asked him if he remained in touch with Sharapova earlier this year, admitting they were “jealous” of him in a question that angered some fans who perceived it as intrusive and irrelevant.
The Bulgarian said he was tempted but unwilling to open up about life with his former partner, who suggested in her autobiography that they had parted because he was a distraction in her pursuit of titles.
Dimitrov reached the semi-finals of the US Open in 2019 but admitted he regretted playing at this year’s tournament, in which he was affected by fatigue after suffering from the effects of Covid-19 for several months.
The 29-year-old was one of several participants to contract the virus after featuring in Novak Djkovic’s controversial Adria Tour event in June.
That was the only tournament he took part in during a break of almost five months in the tennis calendar as a result of the pandemic, although he has still earned just shy of $1 million this year, according to the tour’s official site.