Masha has loved many times and broken many relationships. Some of the Russian tennis player’s relationships lasted only a few days, like with Maroon 5 singer Adam Levine in 2005. There were also people who captured Sharapova’s heart for several years, like Sasha Vujacic or Grigor Dimitrov.

From public to secret, from loving older men to younger men, Masha has experienced all kinds of love adventures. Masha is easily infatuated. Meeting Sasha Vujacic for the first time, she completely “fell in love” with this basketball player. They had a passionate time together with many beautiful memories.

However, maintaining love with a beautiful, talented and rich tennis player is not easy. Sharapova has a strong personality. For that reason, Masha ended her 4-year love affair with Vujacic when many promises were still unfulfilled.

The Slovenian basketball player is said to be too domineering. He likes to control Masha. On the surface, Masha and Vujacic seem happy. In reality, that is not the case. The Russian player himself confessed that he could not stand the pressure from Vujacic, who was quite jealous because his girlfriend was richer and more talented.

“Vujacic always liked to be the center of the universe and control everything. He didn’t remember that I made more money and lived in a bigger house. Vujacic never admitted that I had a more successful career in tennis than he did in basketball,” Masha said in her autobiography “Unstoppable: My Life So Far.”

Vujacic seemed to love himself too much and always thought that his girlfriend needed him more. That made him selfish and pay attention to small things. A year after the two got engaged. Masha and Vujacic broke up in a bad way. The basketball player blamed Masha for not thanking him at the 2012 Roland Garros championship ceremony.

Bored with older men, Masha fell in love with Grigor Dimitrov, who was 4 years younger than her. The Bulgarian tennis player’s sweet messages and sincere feelings were like medicine to heal Masha’s wounded heart. It made her forget about the patriarchal Vujacic. Dimitrov “saw down” Sharapova in this way.

“Why is a handsome guy like you willing to wait for a girl like me who is not ready to date?”, Masha once asked Dimitrov. The Bulgarian tennis player replied: “I will wait. I know what my heart wants, and I want you.” Masha and Dimitrov came together romantically. They shared the ups and downs through each tournament for 2 years.

When Masha’s love for the “young pilot” was at its peak, fate teased the Russian tennis player. Dimitrov, with his handsome looks and youthful vigor, always liked to conquer others. The press rumored that “little Federer” was secretly dating someone else behind Masha’s back. The press said that both wanted to stop their relationship to focus on their careers.

It seems that this is not the case. After leaving Sharapova in 2015, Dimitrov embarked on a love affair with Serena Williams, who is also older than him. In her autobiography, Masha revealed that Dimitrov never considered her the most important woman in her life. Masha’s love life has once again failed.

How to maintain feelings for this beauty is the problem. Not many guys can do that. Many failures in love also make Masha more mature and thoughtful in relationships.

In an interview with Corriere Della Sera , Masha talked about her criteria for choosing a boyfriend: “As long as a man makes me happy, makes me happy, he will have the opportunity to make me want to love again. I like people who surprise me and tell me many unknown things.”

Businessman Alexander Gilkes did it with Masha. After leaving Dimitrov for more than a year, Masha fell in love again with a boyfriend 8 years older than her. The maturity of a middle-aged man helped Gilkes know what Masha needed. Thanks to that, they have been together for 4 years and are waiting for a new chapter in their love.

On February 26, Sharapova announced her retirement at the age of 32, Gilkes hinted at something important that was about to happen to Masha. The media rumored that they were about to get married. If that happens, this would be a happy ending to Sharapova’s love story.