The Truth About Drake And Kylie's Relationship

In the ultimate case of celebrity "are they or aren't they," Kylie Jenner and Drake seem to keep the whole world guessing as to what exactly is going on in their relationship. A close friend of the entire KarJenner clan, the "In My Feelings" crooner has never shied away from an opportunity to gush about the reality TV family. "Everybody's really nice," Drake told E! News in 2013, adding, "The queen of it all — Kris Jenner — she's my favorite. She's the boss."

While it's adorable that the Toronto-born rapper paid homage to the matriarch who, quite literally, started an empire, he also hinted at his dream girl. "I need somebody funny, I need somebody driven. I like unique goals," Drake dished to the outlet. "You know, you talk to a lot of girls and they're like 'oh modeling, acting' ... I like to hear about wanting to be a business owner." Cue Kylie Cosmetics founder and youngest "self-made" billionaire, Kylie Jenner.

Considering Jenner split with baby daddy Travis Scott in October 2019, at the time of this writing, she's definitely on the market. As for Drake? The "God's Plan" singer has been linked to so many different women, he makes Kardashian-Jenner relationship drama look dull. While these two are keeping all of us in the dark with what exactly is going on, let's figure out the truth about Drake and Kylie Jenner's relationship.

Although Drake had already been a KarJenner family friend for almost a decade, it was only in 2019 that the goss surrounding him and Kylie Jenner began to circulate extensively. As sources close to the makeup mogul dished to People in November, Jenner began cozying up to the Canadian artist only one month after her split from Travis Scott. "He and Kylie have been spending time together recently," the source began. "They've been friends for a long time and Drake is very close to the family."

While another insider denied the claims, it certainly didn't keep up with what happened at Drake's birthday bash in late October. According to Us Weekly, partygoers noticed that the Kylie Cosmetics founder was "never too far away" from the birthday boy. "She spent the most time near Drake," one source noted, adding, "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."

Of course, both Drake and Jenner have decided to keep whatever is going on pretty hush-hush (hey, it makes sense for publicity), yet the rumor mill just keeps on grinding. While at the time of this writing, we still don't know much, we're hoping Kris Jenner finds a way to make it all unravel in a new season of Keeping Up With the Kardashians.

For someone still in her early 20s, the amount that Kylie Jenner has accomplished is nothing to scoff at. Having begun her reality TV journey at the young age of 10, by the time she was 18, the youngest Jenner had launched her Lip Kits — what would quickly become her Kylie Cosmetics empire.

Morphing into a businesswoman and mom while still practically a teen herself, the makeup mogul has matured at a rapid rate — which could be why she's chosen to date men much older than her. In fact, her first high-profile relationship was with rapper Tyga, who was famously eight years older than her. The age gap was a topic of controversy, causing the artist to speak to San Francisco radio station 106 KMEL (via E! News) and defend his relationship. "Me being older than her, I've been through a lot more things so I can help her more with it even though she's been more in tabloid media limelight than I have been," he simply explained.

It turns out, Tyga wasn't the only beau in Jenner's life who was older — her ex, Travis Scott, was also her senior — by five years. At the end of the day, perhaps it's Jenner's big sis Khloé Kardashian who said it best to Complex back in 2015: "Kylie might be 17, but from what Kylie has been through and the life she lives, she's not a normal 17-year-old."

Although their flirtation allegedly began in 2019, Kylie Jenner and Drake may have been on each other's radars for a while, as the "Hotline Bling" hitmaker actually met the social media icon all the way back in 2013 — performing at her Sweet 16 bash. In fact, in a now-deleted Instagram post (via E! News), Jenner actually posted a photo of herself and Champagne Papi from the night as he gave her a smooch on the cheek. Fast forward to 2019, when a source told In Touch that the pair have been "flirting for years." Hmm.

Nevertheless, Jenner was certainly too young for Drake (11 years her senior) in 2013, yet he still made cameos at KarJenner events, such as posing for a photo at one of the family's famed Christmas parties in 2015. While the makeup mogul was still with Tyga at the time, who's to say that sparks weren't flying between herself and Drizzy?

By the time Jenner found herself single again after her split from Travis Scott, it looked like insiders could finally give a bit more information as to what may be going on between the TV personality and the Toronto-born rapper. "Kylie has had a crush on Drake since she was a kid, and now he's sexier than ever," a source close to the starlet told In Touch. "The timing for them is finally right."

Kylie Jenner isn't the only person Drake appears to have a relationship with that's much younger than him, in fact, he's raised eyebrows among the masses in the past, too. In 2016, goss rags were abuzz with rumors that the "God's Plan" artist was dating Hailey Bieber (née Baldwin), initially having met her years before when she was just 14. A bit weird, no?

Romances aside, even Drizzy's friendships have come under fire, such as his unexpected BFF status with Stranger Things' Millie Bobby Brown. "I love him, I met him in Australia, and he's honestly so fantastic and a great friend and a great role model," the teen starlet gushed to Access Hollywood in 2018. "We text. We just texted each other the other day, and he was like, 'I miss you so much,' I was like, 'I miss you more!'" While their bond may come across as utterly bizarre, Brown admits he has a bit of a big brother-type role, giving her boy advice whenever he can.

When the "Passionfruit" singer isn't texting the breakout Netflix actress, he has another teen star to message who's at the height of her career: Billie Eilish. "Drake is like the nicest dude I've ever spoken to. I mean, I've only like, texted him, but he's so nice," Eilish told Vanity Fair in 2019. "He does not need to be nice."

Another reason why Kylie Jenner and Drake may want to keep their alleged romance under wraps? Well, considering the "Started from the Bottom" rapper has had an ongoing feud with Kim Kardashian's hubby, Kanye West, it would undoubtedly make family events somewhat awkward.

After diss tracks were thrown back and forth in 2018 (and Twitter wars between the two artists even caused Kimmy K. to get involved), the beef between Drake and West has allegedly died down — although the Canadian rapper shows no signs of fully forgiving and forgetting. "I could never ... turn my back on the things that I've said about him in a positive light, and I still feel all those same things ... Kanye West would be my favorite artist all around. And that's just facts," Drake admitted to Rap Radar at the end of 2019, adding, "Things have just changed. I'm not just some kid that's a fan anymore. Now we have personal situations, and like I said, a lot of his issues with me, I can't fix them for him."

If that's not the only issue, Drizzy would also have to deal with Travis Scott, who's still very active in Jenner's life thanks to their daughter, Stormi. According to an insider who spoke to Hollywood Life, Drake has reportedly even backed off from anything serious because he doesn't want to disrupt the co-parenting dynamic with Jenner and Scott. Atta boy.

Considering Kylie Jenner started allegedly seeing Drake shortly after her split from Travis Scott, chances are, she may simply want to keep things casual. In fact, sources close to both megastars seem to confirm the theory, too.

"Kylie doesn't seem to be dating," an insider close to the Kylie Cosmetics creator told People. "She sees Drake occasionally, but it doesn't seem serious." While Jenner's rep denied the claims to the outlet, we have to remember, the Keeping Up With the Kardashians starlet also rejected claims that she was pregnant (spoiler alert: she was), so everything should probably be taken with a grain of salt.

At the end of the day, these two celebs are both parents and are both focused on raising their children — separately. "Drake and Kylie don't want to jeopardize their friendship by crossing any major boundaries," a source dished to Us Weekly. "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."

Although Travis Scott and Kylie Jenner have, at the time of this writing, broken up, it turns out that the Astroworld rapper still isn't pleased with rumors that Drake may be encroaching on his former territory. As a source revealed to Hollywood Life, "He would feel a bit betrayed if Drake started anything with Kylie ... Travis would still love to figure out getting back with Kylie, so hearing that a friend might be coming on his turf so to speak is a little jarring for Travis to handle." The insider went on to say, "He's hoping and assuming everything was innocent."

So, how does Jenner feel about all of this? Well, when the pair initially split, the reality TV star was reportedly upset her baby daddy wasn't interested in spending more time at home. "He really likes focusing on touring instead of chilling with Kylie and Stormi," another insider dished to Hollywood Life. "Not that it isn't fun for him, but it is something he doesn't always want to do."

That being said, in February 2020, tabs started circulating goss that these two exes may get back together. "They're just being careful because they have to think about Stormi," a source close to the couple explained to Life & Style. "They don't want to get back together and then break up, so instead, they're taking it slow." We suppose only time will tell.

Drake isn't exactly known as someone who enjoys being tied down — meaning it's probably likely that whatever might be going on with Kylie Jenner isn't forever. As a source revealed to Hollywood Life, "As much as people would like for Drake and Kylie to be a thing, it just isn't happening. Drake is a flirt and he has a good time with Kylie when they are around each other but he isn't going to be starting anything with Kylie romantically, all they are is just friends. They will hang out again in the future but right now neither of them are taking it to another level ... Drake is not trying to be in a committed relationship with anyone."

It's a narrative that certainly isn't new for the Toronto-born megastar, as he's "had fun" with Jennifer Lopez in 2017 (who can forget her hair flip and call out during her 2019 tour?) and he's hinted at a fling with Bella Hadid on his Scorpion album, too. Of course, Jenner assuredly isn't blind to Drizzy's past. "She's smarter than that," affirmed an insider to Page Six, adding that the Keeping Up With the Kardashians starlet "isn't interested in a serious relationship with Drake, in part because the rapper is a notorious womanizer." Considering the "trust issues" Jenner allegedly had with Travis Scott, who can blame her?

While Kanye West definitely isn't Team Krake (to be honest, it doesn't have the same ring as Kimye), other members of the Kardashian-Jenner clan are supposedly absolutely on board for a Drake and Kylie Jenner romance. As an insider told In Touch, "Her mom and sisters are encouraging the romance."

It makes sense that Kris Jenner would support the potential relationship — considering it would be a great business move and the woman is notoriously known to work harder than the devil itself. Reporter Joel Golby of The Guardian explained it best, noting that both Kylie and Drake are at the height of their careers, and a high-profile union would only bring more publicity. "Drake has the net worth of a small country, produces the best move-your-a** music of the last decade, has perfect teeth and a litany of supermodels in his sexual history ... Jenner, meanwhile, is slowly morphing into a performance art piece ... Jenner is a sort of moving, breathing Mona Lisa: an enigmatic smile, a quiet stare, a multibillion-dollar lip-gloss line, everything and nothing all at once."

If West and Drake are able to put their differences aside, perhaps the "God's Plan" rapper would feel comfortable getting cozier with Kylie — considering he's already been at intimate KarJenner gatherings in the past and once knew how to play nice with Kim's hubby, too.

While the rumors of Kylie Jenner and Drake pursuing a relationship are still going strong, it looks like, at the time of this writing, what's happening is probably just platonic. As a source told Geo TV, "Drake has definitely moved past any type of romantic feelings towards Kylie and it's purely platonic between them at this point. While there were absolutely some flirtations going on from Drake towards Kylie a while back, it was all in good fun and there was nothing really serious that came out of it."

The Kylie Cosmetics owner is reportedly also enjoying the harmless flirtatious friendship, too, as the single life isn't too concerning for her at this time, either. It turns out, it's the first time in a while that Jenner and some of her siblings are all solo at the same time. As an insider close to the KarJenners told Entertainment Tonight, "Khloe and Kylie (along with sisters Kendall Jenner and Kourtney Kardashian) are actually all enjoying being single at the same time. They all feel complete and perfectly content and are not rushing to get into relationships again."

Of course, the tabs have been lapping up any goss between Kylie and Drake, yet perhaps nothing serious ever happened. After all, it wouldn't be the first time Drizzy has found himself in the middle of Jenner-related goss — in 2015, after being spotted with big sis Kendall, rumors of those two hooking up were going strong, as well.

Although Drake has allegedly been linked to Kylie Jenner since late 2019, he certainly hasn't been hiding the fact that he's been seeing other women, as well. As per Daily Mail, news of the "In My Feelings" crooner dating a new girl began circulating in February 2020, when he was spotted leaving model Imaan Hamman's apartment "in the early hours" after reportedly spending the night together. It wasn't the only time the pair was seen together, either, as Drizzy even attended Hamman's launch of her capsule collection with Frame that same month.

So, is the model the only girl that Jenner may have competition with? Well, not quite. If seeing Hammam wasn't enough, there have also been reports of the Toronto rapper spending time with his ex, Rihanna, too, after her split with Hassan Jameel in January 2020. According to Hollywood Life, the celeb superstars were spotted "getting cozy" together at an A$AP Rocky concert in New York — the day that RiRi's breakup with Jameel was announced. Considering Rihanna once told Vogue in 2018 that she and Drake weren't friends anymore, we're assuming that's all water under the bridge.

After all is said and done, while some Jenner and Drake fans are hoping for a relationship to come out of whatever is going on, we won't hold our breaths. If the Kardashian-Jenners are good at one thing, it's keeping the rest of the world guessing.