Novak Djokovic took Maria Sharapova on dinner date as a bet after winning match

Novak Djokovic once attempted to woo Maria Sharapova with a cheeky bet that ended with the tennis duo going on a date. Keen to impress the Russian when they were both breaking through on their respective tours, Djokovic took her out to a Japanese restaurant in the weeks before an Indian Wells tournament.

Now happily married to wife Jelena Ristic since 2014, Djokovic once had eyes for a date with Sharapova. Both players were impressing in the early stages of their tennis careers. Ahead of Indian Wells one year, the 24-time Grand Slam winner wanted to take things one step further. Djokovic saw his opportunity while they played at an exhibition in La Quinta, and bet Sharapova that if he won his match, he would take her on a dinner date.

Speaking in 2020 during a live stream on Djokovic’s Instagram, Sharapova recalled: “I think we were playing a mixed doubles against each other and you said that if you win, I would have to get you dinner, and I was like, ‘OK, whatever. Who is this kid?’

“And you won and you’re like, ‘We have dinner, tonight. We are going to the Japanese place’. I was like, ‘Are you serious? You and me, going to dinner? Tonight?’ So we did. We ended up going to dinner.