Grigor Dimitrov, the Bulgarian tennis sensation, is not just known for his powerful performances on the court but also for his intriguing dating history with some of the most accomplished and influential women in the world. Once regarded as an upcoming gem in the world of tennis – fit to follow in the footsteps of tennis’ Swiss Maestro – the Bulgarian heartthrob has heavily fronted headlines over the years for his high-profile dating life.

From dating the tennis legend Maria Sharapova to international heartthrob Madalina Diana Ghenea, the list only gets bigger and bigger. From power couples to glamorous love stories, Dimitrov’s dating life has never failed to capture fans’ attention. Here is a list of some of the most captivating sensations that he has crossed paths with.

Grigor Dimitrov and Maria Sharapova: The power couple

Grigor Dimitrov’s relationship with Maria Sharapova marked a defining moment in his personal life. The two tennis stars became one of the most formidable power couples in the sport. The two started dating back in 2012. However, it was only in 2013 that the two came out publicly.

However, the relationship was one of complete ups and downs and after 3 years, the two decided to part ways at Wimbledon in 2015. In her autobiography released in 2017, Maria Sharapova revealed the real reason behind their split. She suggested that at that time, she was more career-oriented and focused on her achievements rather than being someone who gave more time to the relationship.

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“He pulled out a book that Wimbledon puts together of previous championships,” Sharapova said. “He quietly flipped through the pages of the book until he found a picture of me, in his box, watching his match. He looked at me, sad – I thought I saw tears in his eyes – ‘Did you see this? This means everything to me. Seeing you in my box next to my mother,’” she added.

“It was then, at that moment, that the emotional pull I had been fighting came to an end. I knew, and so did he, that I couldn’t be that person at this time of my life. I was supposed to be focused, getting prepared for my own matches, my own triumphs and defeats, on the largest stage of my career,” Sharapova continued.

Bulgarian ATP Heartthrob Grigor Dimitrov Dons His Playful Side With 35-Year-Old Romanian Girlfriend as They Become ‘Happy Kids’ Again

And thus, their love story came to an end. However, after their mutual split up, Grigor started a new dating life as the rumors of him dating an American crooner came to life.

Grigor Dimitrov dated American songbird, Nicole Scherzinger

Another chapter in Dimitrov’s romantic journey was his relationship with American singer Nicole Scherzinger. In an interview, the Bulgarian player revealed how she helped him get over his ex-girlfriend Maria Sharapova. He suggested that at a point where everything seemed to have fallen apart, she was the one who took all the pieces together and fixed them.

He even suggested that despite their busy schedules, she did a fantastic job of supporting their relationship and him by managing to go to places where he was playing despite having a full schedule of her own. “The schedules are very heavy. But she’s doing a better job than I am at being able to come to most of the places I’m at,” he said in an interview.

However, their dalliance was also short-lived and the two decided to part ways, eventually. Back in 2018, there were strong rumors of the couple breaking up before finally in 2019, the couple split up. Soon after this chapter, Dimitrov decided to move on and found love in a Russian heiress.

Bulgarian heartthrob meets Russian heiress

Dimitrov’s dating life took an international twist when he crossed paths with Russian heiress Lolita Osmanova. Their relationship added an element of glamor, as the Bulgarian heartthrob and the Russian heiress brought together their unique backgrounds and experiences.

The daughter of a Russian billionaire, Osmanova had been married to another man. However, as they parted ways in 2018, she found love again in Grigor Dimitrov. The couple started dating in 2020 and their fans found confirmation of it after a social media post of the couple went viral.

But, just like any other case, their relationship was also short-lived. This came to many’s notice when the two were not spotted together for quite a while. Adding to this, his girlfriend’s revelation about their relationship on social media led many to wonder that the two were no longer together. Consequently, soon after that, many started to assume that the Bulgarian heartthrob had replaced her with an international heartthrob, Madalina Ghenea.

Dimitrov meets another international heartthrob

The final chapter in this romantic journey takes us to Dimitrov’s involvement with the international heartthrob Madalina Diana Ghenea. The Romanian actress was often spotted with the Bulgarian player. The two came into the headlines when Ghenea made it to the player’s box when Dimitrov played against Carlos Alcaraz in the Madrid Open. If the reports are to be believed, they both started dating back in April this year.

However, in recent days, the rumors of the two parting ways have been highly speculative. But nothing conclusive has come to light. That being said, the fans are still assuming that the two are still together and having a great time.

Thus, Grigor Dimitrov’s dating life has seen some of the most influential women from various fields. Not only this, his dating life has been nothing short of a rollercoaster journey. While he continues to cause havoc on the tennis courts, his fans are hoping for him to find his one true love and settle down. But it is only time that will reveal what happens next.

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