Drake and Williams have been pals since 2011 and have collaborated on several projects together. Drake is also secure enough in himself to step on the court and play tennis alongside Williams, which is a bold thing to do.
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However, in the fall of 2011, rumors started spreading about Drake and Serena Williams following a tweet from Drake to Williams which says; “@serenawilliams I cannot wait to put it on you and make you sweat……….during our match this weekend.”
Despite all of the speculations and suspicions that Drake and Serena Williams are dating or engaged, they have not publicly acknowledged their connection. Even though they had some nice times together, Drake’s friendship with Serena Williams did not endure.
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We're witnessing the early stages ❤️❤️ pic.twitter.com/dOEscFJ0nt
— mp (@friasmp) August 24, 2015
Serena Williams later announced, Alexis Ohanian, co-founder of Reddit, as her boyfriend shortly after Drake’s 29th birthday in October 2015. This means that Serena Williams and Drake are not engaged.