Many fans believe that Drake has been romantically involved with a number of the Kardashian-Jenner sisters over the years. Keep scrolling to find out which members of the famous family he’s been linked to, learn about the dating rumors and more.

How Long Has Drake Known the Kardashian-Jenners?

The “Nice For What” rapper has been linked to the famous family since he performed at Kylie Jenner’s Sweet 16 birthday party in August 2013.

As the years continued, Drake remained part of their lives and collaborated with Kim Kardashian’s then-husband, Kanye West, on several songs beginning in January 2015.

In December 2015, the Degrassi alum seemed to solidify his standing among the sisters when he attended the annual Kardashian family Christmas party.

“Me, my mom, and a photobomb,” Kylie captioned a photo with Kris Jenner and Drake from the party.

Did Drake Hook Up With Kim Kardashian?

Rumors began to swirl that Drake previously hooked up with Kim when the Canada native seemingly referenced her by using her nickname “Kiki” in his 2018 song ​​“In My Feelings.”

“Kiki, do you love me? Are you riding?” he sang in the song.

The song was released amid his falling out with Kanye, whom Kim was married to from 2014 until 2022. At the time, the rappers were feuding after Drake accused Kanye of telling Pusha T about his son. Pusha T then revealed that the “God’s Plan” hitmaker had welcomed his only child, son Adonis, in 2017. However, Kanye has denied leaking the information.

Despite the speculation that Drake hooked up with the SKIMS mogul, Kim shut down rumors by telling fans that it “never happened” via Instagram in September 2018.

Kim further opened up about how Kanye spreading the rumor about Drake, as well as other comments he’s made, hurt her during the May 25 episode of The Kardashians.

“The one that was supposed to protect me—and still does interviews saying they will be my forever protector—is the one that’s hurting me the most,” she told Kris. “He was the one that started a rumor that said I was hooking up with Drake, having an affair. Our whole marriage he accused me of that publicly.”

She added, “I really can’t wrap my head around how he thinks he is a protector.”

Did Drake Date Kylie Jenner?

Another Kardashian-Jenner sister that Drake has been linked to is Kylie.

In October 2019, a source told Us Weekly that Kylie “never too far away” from Drake at his 33rd birthday party.

“Kylie was rapping to songs and dancing with her friends while she was next to Drake, but they weren’t dancing together. They seemed to have a connection though,” one source shared, while a second insider added that the pair were “enjoying each other’s company.”

The second source continued, “They were joking around and Kylie was laughing. She seemed to be really happy and in a great mood. And [she] and Drake seemed very comfortable with each other. There seemed to be an attraction there.”

The following month, an insider told Us Weekly that Drake and Kylie’s friendship has turned romantic.

However, the relationship never seemed to take off and neither Drake nor Kylie have confirmed that they were ever in a romantic relationship.

Did Drake Hook Up With Kris Jenner?

The most surprising Kardashian-Jenner that Drake has been romantically linked to is Kris.

In October 2022, Kanye claimed that Drake hooked up with the matriarch in a now-deleted Instagram post. “DRAKE A F–K YA BABY MAMA’S MAMA,” the “Gold Digger” rapper wrote at the time. “THAT’S REAL WAR.”

Did Drake Date a Kardashian-Jenner? Find Out Which Sisters He’s Been Romantically Linked To
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Later that month, Kanye repeated the claim when he appeared on the “Drink Champs” podcast. “Yeah, that was hard,” he said about the alleged affair.

However, neither Drake nor Kris have publicly commented on the rumor.

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