• Kylie Jenner and Drake sparked dating rumors at the rapper's 33rd birthday party in October, where the two were apparently "attached at the hip."
  • Multiple reports have suggested a connection between the two during the star-studded affair, although not much concrete evidence lends itself to the dating rumors.
  • Other A-listers who attended the event include Adele, Future, and Snoop Dog.

Apparently, nothing is impossible when it comes to Hollywood romances, since 22-year-old makeup mogul Kylie Jenner is now rumored to be sparking a connection with 33-year-old musician Drake.

During the rapper's birthday party at Goya Studios in Hollywood last month, Jenner and Drake reportedly appeared to be into each other, according to multiple outlets. Now, a new report alleges that the two have been spending time together "romantically." Keep reading to see what's really going on between Drake and Jenner.

Did sparks fly at Drake's birthday party?

A source at Us Weekly said that Jenner "spent the most time near Drake and his friends." The source added, "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."

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A different source for the outlet also said, "They seemed to be enjoying each other's company. They were joking around and Kylie was laughing. She seemed to be really happy and in a great mood and her and Drake seemed very comfortable with each other. There seemed to be an attraction there."

Another source for Page Six said that they saw Drake chatting with both Jenner and Corey Gamble "for a while," although it may have been more of Drake's star hosting abilities rather than his romantic connection with the Kylie Cosmetics founder.

"He was actually the quintessential gentleman," the source told the outlet. "He greeted people and said hello to everyone and shook hands. He really had a good time with his friends and was laughing … He literally worked the room for the entire party."

The dating rumors come less than a month after Jenner split from baby daddy Travis Scott, although the two are reportedly on good terms.


What happened after the party?

According to People, an inside source revealed that the two have been hanging out "romantically" since she split from Scott.

"He and Kylie have been spending time together recently," the insider said. "They've been friends for a long time and Drake is very close to the family."

Don't ruffle your feathers just yet; another source for the outlet countered these claims of romance, stating that the two are firmly "just friends." And a third source also continued to deny the dating rumors.


Since when have they seen each other romantically?

A source at Us revealed that Drake has apparently "always had a thing" for Jenner, although their relationship "isn't anything serious."

"Drake has always had a thing for Kylie and it's mutual," the source said. "They hang out here and there and have been more recently than in the past because Kylie is technically single right now and the two of them live so close to each other."

Still, their relationship is murky.

"They have known each other and been friends for a very long time and there has always been a spark there, but their situation is complicated and so is Kylie's with Travis," the source said, referring to Jenner's recent breakup with Travis Scott.

"Drake and Kylie don't want to jeopardize their friendship by crossing any major boundaries. Drake doesn't have any intention of taking on a fatherly role with Stormi and he wants to have fun with Kylie with no strings attached and continue to have a friendship and be supportive of one another."


Are they dropping hints about their supposed fling?

A new Instagram photo of Drake has fans speculating once again. The rapper uploaded a selfie of himself in a sweatshirt from Sierra Canyon, the school that Jenner attended as a child, and a baseball cap with a lip imprint on the front, possibly a nod toward Jenner's famous lip kits.

He captioned the suggestive photo simply with, "💋."

Jenner, too, possibly dropped hints on her own Instagram by posting a photo of seemingly innocuous vending machines at the Kylie Cosmetics HQ.

On one side is a bubblegum-pink Skittles vending machine, and on the other is a champagne vending machine. For the uninitiated, Drake's nickname is Champagne Papi. How much more obvious can these two get? A lot more obvious, actually.

Headshot of Chelsey Sanchez
Chelsey Sanchez
Digital Associate Editor

As an associate editor at HarpersBAZAAR.com, Chelsey keeps a finger on the pulse on all things celeb news. She also writes on social movements, connecting with activists leading the fight on workers' rights, climate justice, and more. Offline, she’s probably spending too much time on TikTok, rewatching Emma (the 2020 version, of course), or buying yet another corset.