In the music industry, Drake has been known to be a womanizer of some sort. He has dated high-profile celebrities and people in the industry, and he has gained a significant reputation.
Although he has remained non-committal most of the time, Drake has had plenty of women.
Did Drake & SZA Date?
As revealed in his song "Mr. Right Now," Drake claimed that he and SZA previously dated in 2008. However, SZA clarified their dating phase, saying it was actually 2009.
"So It was actually 2009 lol ... in this case a year of poetic rap license mattered lol," she revealed. "I think he jus innocently rhymed 08 w wait. Anybody who really knows me and was around during this time can confirm ... it's all love all peace."
SZA also discussed her relationship with Drake in a 2022 interview with Audacy.
"We're cool, we've always been cool. It's never been weird," she added. "Anytime he's ever mentioned me, it's always been positive. He never said anything negative about me, and I'm grateful for that. I think really highly of him ... I'm an artist now, I wasn't then, and he's King Drake!"
The two recently linked up with Sexyy Redd on "Rich Baby Daddy."
Drake Got Cozy With Hailey Bieber
At one point, Drake reportedly got "cozy" with then Hailey Baldwin. It happened during an off-period with Rihanna.
"They were having a lot of fun together and were very affectionate," a People Magazine source said, referring to the two getting "cozy" at a Memorial Day party in 2016.
In the end, Hailey went with another Canadian and married Justin Bieber.
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Drake, Kylie Jenner Dating Rumors
Around 2019, it has been heavily rumored that Drake and Kylie Jenner had a fling.
A People Magazine source revealed that Drake and Kylie got their "once-platonic relationship to romance."
"He and Kylie have been spending time together recently. They've been friends for a long time and Drake is very close to the family," a source divulged. However, another later said they were not in a relationship despite their chemistry.
Drake, Rihanna Relationship
For ten years, Rihanna and Drake engaged in an on-again, off-again relationship - making each other's most high-profile relationship.
The two were on the fences with each other in their earlier days. In the 2016s, the couple made their relationship more public and even gave more extensive displays of affection.
However, in 2018, Rihanna revealed to Vogue that she and Drake "don't have a friendship now."
Meanwhile, Drake spoke "warmly" about his relationship with Rihanna in 2018 to LeBron James' "The Shop."
"As life takes shape and teaches you your own lessons, I end up in this situation where I don't have the fairy tale, like, 'Oh, Drake started a family with Rihanna and this is like so perfect.' It looks so good on paper. By the way, I wanted that too at one time."
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