“I saw tears in his eyes,” Maria Sharapova wrote in her autobiography Unstoppable (2017), recalling the time when she sat in Grigor Dimitrov’s player’s box alongside his mother, turning the Bulgarian star extremely emotional. The relationship eventually didn’t work out, as both of them had different career goals, but until they were together, they were making headlines quite consistently. Now, almost a decade after their break up, Dimitrov has revisited his relationship with Sharapova during the ongoing Miami Open. So, what has gone down?

It won’t be an overstatement to say Dimitrov is one of the most eligible bachelors in Miami right now! After surprising a lucky fan with a special rose delivery a couple of days ago, the 33-year-old joined two female fans on a cable car ride. And, during their interaction, the fans asked him to describe his “dream girl.” Later, he was asked to name one female player he would want to get hitched with.

Dimitrov hesitated for a bit initially saying, “Marry? Putting me on the spot here.” But once he was pushed, he came up with a counter-question. “Yeah because I’m not ready for marriage. Who do you think will be a good fit for me to go to dinner with? Let’s see that.”

“Maria Sharapova,” the answer was quick and predictable. Dimitrov gave a cheeky smile and said, “She was my ex-girlfriend.” The fans apologized straightaway for making this awkward, but the Bulgarian laughed and replied, “It’s all good we’re on excellent terms.” When did Dimitrov start dating Maria Sharapova though?

Well, they got together in late 2012 and made their relationship public during the 2013 Madrid Open. However, two years after that, they had broken up. Dimitrov has been linked with several names ever since, including Lolita Osmanova, Madalina Ghenea (Romanian actress), and Ekin-Su Culculogu (‘Love Island’ reality TV show winner) but he is yet to marry.

Before Sharapova, there were rumors of Dimitrov’s relationship with the American legend Serena Williams as well. But neither of the two ever confirmed it. Last year, during the Miami Open, Serena Williams was even spotted attending one of his matches. When Dimitrov was asked about it, he said, “Yeah, she’s amazing. We stay in touch. We nearly speak on a daily basis. She was like, ‘I’m going to come watch.’ I was like, ‘Okay.’…My friendship with her means so much to me. I remember she was even here when I had my first top-10 win. It’s friendship, man.” But why did Dimitrov break up with Sharapova?

When Maria Sharapova and Grigor Dimitrov revealed the reasons behind their split

On 26 February 2020, Maria Sharapova announced her retirement from the sport and Grigor Dimitrov was among the first ones to share a heartfelt note for the Russian. “There’s so much I can say, [though] it’s not the place for me to say much. Maria is who she is. Nothing but love and respect for that person. We’re great friends,” said Dimitrov. Later that year, Sharapova got engaged to British business Alexander Gilkes and in July 2022, she gave birth to their son, Theodore.

Talking about his relationship with Sharapova in an interview with The Telegraph in 2015, Dimitrov said, “We were both in China, me in Shanghai, her in Beijing. I sat down for lunch and saw her playing on television and emailed right away. We started talking a bit, and then a month later when the season was over we saw each other and that became that. Sometimes I just go crazy and send her hundreds – 500 is the most I’ve ever sent at once.”

But what did Sharapova have to say about their relationship? Well, in her autobiography, the Russian cited the timing of their relationship as the biggest hurdle. “I was supposed to be focused, getting prepared for my own matches, my own triumphs and defeats, on the largest stage of my career. I had been watching his match that day only because I’d lost early at those championships. So his good memory was my bad memory. What meant everything to him happened only because I had lost,” she wrote.

Mid-2016 was not a great period for Dimitrov. After splitting with Sharapova, he also parted ways with his coach, Roger Rasheed. Recalling that phase in one of his old interviews, the Bulgarian once said, “I stopped with my coach. I lost my ranking. I basically sucked at tennis I was fighting with people and I went through my break-up. I was tired of everything, one by one, falling apart.”

Basically, both Dimitrov and Sharapova chose to part ways to focus on their first love, i.e. tennis and that’s how this beautiful love story came to an end.