For the longest time I despised everything there was about Novak Djokovic. He was this cocky, arrogant, ruthless motherfucker who was comfortably ok with being THE villain of the sport. To be honest, he never really did anything wrong other than stopping the primes of Federer and Nadal. There have been some quotes that lack self awareness and some corny moments, but for the most part the constant beating up of tennis legends is what branded him as this terrorist to the fans.

To his credit, Novak fed off that hate and didn’t stop until he became the GOAT of the sport. He took EVERYONE out. Djokovic ran through multiple waves of young talented players, chewed em’ up, and spit them out like it was nobody’s business. It took until the last year for someone to finally arrive in Carlos Alcaraz to challenge him.

I have to admit though, since Fed’s retirement I’ve come to not hate Novak as much. I’ll even go as far to say I appreciate how great he is, and this story from way back adds a bit more to his legacy off the court.

Cocky young Novak just entering his 20s finding a way to take Sharapova out to dinner? It’s that kind of confidence that’s required to reach the level in the sport that he has. I’m just picturing Novak trying like 200% during this exhibition, sweating his balls off to win this bet. Treated it like a grand slam final. When date with Sharapova is on the line the stakes are that high.

And sure the story that’s told describes it as just a dinner.

Factor that bet/dinner story into the equation with this video of them going back and forth? You do the math.

Certainly not assuming anything, but hey all these attractive people are on tour together for like 10 of the 12 months of the year, you never know! He was technically dating his now wife Jelena back then, but they weren’t engaged.

Novak, today I tip my cap to you.