No, because I can’t be the only one who thinks Drake’s dating life is still so cringe

On the rapper’s infamous history of romantic faux pas, the irony of high-profile women avoiding him like the plague, and why celebrity couples occasionally fascinate me.

Sydney Nicole Sweeney
10 min readJul 19, 2021
So much for private time! Photo by Chris Cristi.

The other day, rumors started swirling that Drake has a new gal pal. Her name is Johanna Leia and she has an ass (BBL?) worthy of Twitter discourse. Almost thicker than her butt, though, is the stack of cash Drake must have needed to take Leia on a Friday night dinner date to a desolate Dodger Stadium, which is precisely what he did last week.

What kind of person would equate such a grandiose gesture to true romance? I have no idea. Personally, I’m just fine with a date night comprised of mid-tier sushi, splinters from equally cheap chopsticks, and six-dollar, pre-made Bellini from Trader Joe’s. But who am I to speak? There is no telling what I would find tasteful if I were whisked away from my peasantry and laced up in Leia’s high-heels: those of a fortysomething woman with the perplexing title of “entrepreneur” in her Instagram bio and an obvious, contractual obligation to post sponsored thirst traps in fast fashion garb.

To make things clear, I hardly care about Drake more than the average young person. (Unless we’re talking about Drake in the context of Degrassi, in which case I will never not talk about his thespian transcendence as Jimmy Brooks. He went *there*.) I’m super disgusted, actually, that for the sake of a mildly entertaining story lede I had to pseudo-simp for Drake the Rapper for even a few seconds — as if the thought of being reincarnated as someone he would date is worthy of my daydreams.

However! I am interested in the dating life of Drake mostly because I’m interested in women. The life choices — or, in this case, mistakes—we make. I’m almost positive dating Drake is a certifiable lapse in judgment. Like, yeah, I’d love to believe no woman would want to be that secondhandedly embarrassed bitch on the other end of the line in “Marvins Room,” yet I’m almost positive that’s the exact type of bullshit endured by any chick who’s touched Drake’s ding-dong in their past. If he’s unabashedly corny in his best-selling, artistic oeuvre, a very public matter, he’s definitely worse in a private one: his strange, random dating history, in which the only consistency is that women you’d expect a man of his status to cuff up with—female dignitaries with not necessarily equal but still comparable fame, fortune, and creative interests, perhaps—never want to date him. Ever.

Sure, that’s a harsh, slippery slope to scoot down. But Drake, himself, hasn’t ever hesitated to call attention to his inability to hold down a conventionally famous woman down. I’ll elaborate more on this later (screw a perfectly structured essay, I’m writing this for free), but first, let’s take a stroll down memory lane. In 2017, we all bellowed a collective “Who?” upon learning the mother of his child (“What????? Drake has a baby???”) was a regular woman named Sophie Brussaux, a not-famous former porn actress. (She’s a painter now, by the way, which is lovely.)

Then you have Leia, the woman who’s reportedly Drake’s current boo thang, another ordinary individual. I mean, the internet would tell you differently — she used to be on a one-season-wonder Lifetime program called Bringing Up Ballers because her son is supposedly a teen basketball prodigy. (Reports also say Drake is mentoring the kid, which is expected, because what naive teenage boy wouldn’t want to be counseled by a corny f*ckman?) But in 2021, being a canceled-reality-show star—or even an IG influencer with a Range Rover, McMansion, and “entrepreneurial” dealings with Fashion Nova—isn’t quite the fast track to achieving classic household-name status. And none of this is to say getting on Drake’s pop-cultural or economic level is Leia or even Brussaux’s shared aspiration; Brussaux just wanted child support and Leia just wanted to be taken out to the ballgame sans ballgame. But facts are facts. The chicanery of Drake is he’s over-sentimental but iconic. So it’s both hilarious and sort of sad he can’t seem to bag a lady whose social CV is as impressive as his.

On Scorpion, Drake’s fifth album, there’s a track titled “Jaded.” Lyrically, it’s as bitter as its name suggests; the 34-year-old rapper broods about a younger woman who used him (for her own career), broke up with him (over text), and ended up with a guy not unlike him (“I need to know how the new nigga you got does the same thing I do for a livin’”). According to probably true gossip, the 2017 track’s female subject is 24-year-old R&B sensation Jorja Smith, who was reportedly romantically involved with Drake that year when he plucked the songstress out of indie obscurity to collaborate with her for More Life. I find something deliciously juicy about the saga of Drake and Smith, mostly because I’m a Regular person who lives for tea steeped between two Famous musical artists I casually fuck with. But even for a nosy b like me, “Jaded” is way too transparent in its references: the female subject’s music career, where she’s from, her age and new relationship.

You don’t have to stan either singer to know who Drake is waxing salty about, and that fact is absolutely cringe —ironic, even, when you consider their respective ages at the time, roughly 30 and 20. In what’s basically the sonic form of a viral, angsty Tumblr post written by someone Smith’s age, Drake, a grown-ass man, airs a funky load of dirty laundry. Smith, on the contrary, remained unbothered and hot, releasing a heartbreak single that could be about Drake as much as literally anyone else. Is it shocking who showed their ass in this story? No; men are fools at any and every age. But a decade into adulthood, you’d think Drake would have learned at *least* the basic motions of common sense as it relates to romance and stardom: No woman with their shit together wants the intimate details of their business aired out involuntarily. I mention Drake’s fiasco with Smith first because it’s the most recent, obvious example of the musician’s self-inflicted mess of a love life. However—surprise, surprise—“Jaded” isn’t even his worst tomfoolery, because Rihanna, of course.

Twenty-sixteen was a tragic year on all fronts. But just months before shit really hit the fan, Drake kicked off the American Rapture with his unforgettable, four-minute speech at the 2016 MTV VMAs, sharing with 6.5 million viewers that he was—and had been for many, many, many years—in love with Rihanna, the most unattainable woman in the world. Everyone’s first thought: “Haha, aren’t we all!” Everyone’s second thought, upon realizing he was deadass: “Boy, if you don't get your ass up off this stage.”

Two years after his sprung spiel, Rihanna admitted to Vogue she could have done without the entire thing, describing the experience as “uncomfortable”—a sentiment you could see via her body language as she stood on stage with arms crossed, rolling her eyes, pursing her lips, and, at one point, turning away from the audience as if she was ready to say “eff it” to her fancy award and bounce altogether. The gag is that Drake didn’t just confess his endless love for Rihanna in the most public of industry spaces, an award show; he also claimed to be long-time besties with the Barbadian icon. Yet, his decision to call a superfluous amount of attention to Rihanna (even in an award show setting, where it’s pretty darn hard to kiss too much ass), was the kind of stunt a fanboy-ish stranger would pull. “Waiting through that speech was probably the most uncomfortable part,” she reflected to Vogue in 2018. “I don’t like too many compliments; I don’t like to be put on blast… We don’t have a friendship now, but we’re not enemies either. It is what it is.”

That night, watching Drake was quite like watching a loser boy strategically ask a hot, nice girl to prom in front of the whole cafeteria. He knew she would say no if no one were watching, so he made a private conversation—something that could have been sorted out over text or a nice dinner—a town-hall orate Rihanna had no choice but to react to with civility and kindness. And even this analogy implies the VMAs speech was the first time Drake had tried it. Apparently, Drake continually failed to sell himself to RiRi numerous times before, so we can only assume such failures inspired him to go public on the SSE (Simp Stock Exchange).

A screenshot of an Instagram selfie-style photo where J.Lo and Drake are both smiling at one of her concerts.

But aside from sabotaging his future with one of the baddest bitches alive, Drake was taking Ls with other notable women: Jennifer Lopez, who he reportedly dated right before jet-setting to Amsterdam, where he linked up with (and impregnated) Brussaux (he vaguely rapped about the fling in his 2018 single “Diplomatic Immunity,” too); Tyra Banks, with who he went on a singular date in 2012; Serena Williams, who he was definitely caught smooching on multiple occasions back in 2015; or, in 2018, British songwriter Raye, who’s penned tracks for John Legend and Beyoncé. You could say I’m sensationalizing the demise of these escapades; I know why they ended as much as the next, meddlesome pop-culture enthusiast who spends too much time lurking on Reddit and line-reading on Genius. But the record shows if Drake can very clearly screw things up with women like Smith and Rihanna, he has an entire closet of skeletons.

Still, none of his failed, high-profile relationships—cautionary tales, if you will—have prevented others from involving themselves with the rapper. I say “involved,” because the mother of his kid wasn’t actually *dating* him; apparently it was a one-night-stand thing. Can you entirely blame her? Drake isn’t not attractive. You’d think embracing a Drizzy booty call would be a smarter move than committing to his emotional ineptitude—but even that resulted in a bigger (baby-sized!) issue. (Perhaps his dick is cursed?) Leia, on the other hand, is more than “involved” with him; rumor has it they’ve been together for months.

A photo of influencer Johanna Leia sitting on a bed in a Fashion Nova outfit: a neon yellow lace bra and matching underwear and arm sleeves. The post is sponsored.

And that’s what I’m really perturbed by: After all the red flags Drake has staked into his dating history, he still has some pull. Although traditional celebrities have seemingly hit the ground running after the whole Smith debacle—four years later and he still hasn’t been linked with another A-lister—medium-profile women still view the rap mogul as a viable option. Call me a hater (I am), but this doesn’t… surprise me, per se. Any chick who is on a grind comparable to Drake’s (be it creative, entrepreneurial, or athletic) ironically doesn’t have time for Drake. His corniness. His immaturity. The endless group-chat roast that would catch fire if her clique of equally ambitious girlfriends found out she even considered dating him (a thoughtcrime).

All this is to say that Drake’s dating life is a bummer. I know it’s his fault. I know that if Drake weren’t who he was—a simp, a screw-up, a clown—he wouldn’t be the hit-maker he is. Even 11 years after his debut album propelled him to success, he’s known to date as that “sensitive” rapper, which is really just an enabling euphemism describing a male artist in desperate need of therapy. But in my pop-culture dreams, Drake’s propensity to embarrass himself in the romance department is exclusively a persona—sort of like how The Weeknd still broods about dope and f*cking random bitches as if his supply of pussy and pills is as unpromised as tomorrow, despite having serious relationships with what appear to be level-headed women like Selena Gomez and Bella Hadid and noting that drug use is more of an “occasional” interest, these days.

But this is real life, and here, Drake sucks within and beyond the booth. Surely it would be cool and even inspiring for the global superstar to date someone who’s at least as influential as him on paper, someone who would allow him to join the ranks of pop-cultural power-couple-hood with other icons who don’t even need surnames: Beyoncé and Jay-Z; Kanye and Kim (R.I.P.); Will and Jada; Gabrielle and Dwayne; Uzi and JT; hell, even Harry and Meghan. However basic it sounds, celebrity couples mean something, even if you act like you’re “above it.”

In the culture, these dynamic duos represent the harmony of immeasurable success and bountiful love — two things a lot of us want—experienced by the people we admire and sometimes envy, overtly or secretly. These romances also throw us a bone of escapism: an IG post, a red-carpet appearance, a creative collaboration, a tabloid shot, a rumor to chatter about when we want a moment away from our own bullshit. So when someone like Drake—talented, good-looking, wealthy, generally likable—has made excellence his brand, a mediocre love life simply does not suffice. Get that shit together, Aubrey.



Sydney Nicole Sweeney

Sydney Nicole Sweeney is a journalist based in Los Angeles.