Two months later, now approaching the season's last Grand Slam, the U. Not only was Drake in the crowd cheering Serena on, as he was at the Rogers Cup in Toronto the week before, he wined and dined her after the match at one of Cincy's fanciest restaurants.They had a private room in the restaurant, and were reportedly joined by six others, but the room wasn't private enough, as restaurant-goers were able to catch some snapshots of the two getting awfully close.
In summer 2011, Drake sent out a highly suggestive tweet to Williams and the two were soon pictured together on the court.
Drake's initial contact with Williams led to a beef with Chicago rapper Common, who had previously dated the tennis champ. Open, where Williams looks to become the first winner all four Grand Slams in the same calendar year in 27 years.
The beef wasn't quite as sensational as, say, that of Drake and Meek Mill, but Drake was willing to go to war for Williams then, and, now, four years later, the pair seems to be even more of a winning combination.
The rapper turned renovation show reality star - charged with burglary and grand theft after allegedly pilfering property from a foreclosed home in Palm Beach, Florida - seemed teary as he said he has barely eaten or slept since turning himself into police on Wednesday.
'I'm sorry to everybody': Vanilla Ice gave his first proper interview since being released from lock up earlier this week while leaving Florida on Friday bound for Columbus Ohio.