Grigor Dimitrov is currently dating Russian heiress Lolita Osmanova. Osmanova is the daughter of a wealthy Russian businessman, Eldar Osmanov, who owns energy sales holding company Mezhregionsoyenergo.

The pair have been dating since late 2020. Osmanova is the CEO of Luxury International Magazine, which is published monthly in 8 countries. 

Osmanova was previously married to Gaspar Avdolyan. The couple had a grand $10 million wedding at the Dolby Theatre in Los Angeles that featured a giant golden cake and a performance from Lady Gaga.

Since 2015 Dimitrov was dating Nicole Scherzinger, an American singer, songwriter, and TV personality.  Dimitrov talked about having kids with  Scherzinger but their busy schedules made their relationship difficult.

Dimitrov previously dated Maria Sharapova for 3 years. Prior to that, he dated Serena Williams for a short time.  

Dimitrov comes from a sports family – his father is a tennis coach and his mother, a former volleyball player.  He reached a career-high ranking of world number 3 in 2017. He reached the semifinals of a grand slam three times his career. He is the highest-ranked Bulgarian player in history. He is also the first Bulgarian man to win an ATP title.