What's Up With Drake Texting Teens?

Both 17-year-old Billie Eilish and 15-year-old Millie Bobby Brown have said they text with the 33-year-old rapper. What are we to make of this?
Rag Time is a regular investigation into the stories you see in the tabloids, with the context you don’t.

Last week, Drake, 33, posted a photo of himself on Instagram wearing a hoodie emblazoned with the words "Sierra Canyon." For those unfamiliar: Sierra Canyon is not a vacation destination or a liquor company or some other luxury brand that Drake is promoting. It is a high school. The children of famous people go there, like Lebron James' son Bronny James. (He plays on the basketball team, which is apparently pretty good.) Kendall and Kylie Jenner also went there. Drake, it turns out, did not go there. So why was he wearing the hoodie?


Some people think that Drake is a fan of the Sierra Canyon basketball team, and that he posted the photo on Instagram to show his support for Bronny. Others think Drake wore the high-school merch to signal his romantic interest in Kylie Jenner. Either way, Drake's devotion to this particular high school gives us an opening to discuss a related issue, which is that Drake likes to talk and text with teenagers.

Since Stranger Things actress Millie Bobby Brown, 15, revealed last year that Drake had struck up a texting relationship with her, the tabloids have not quite known how to handle this information. Yes, Drake used to attend high school and also played a high-schooler on TV. But now he is 33. What are we to make of this? Let's assess the available evidence.

"Why u gotta make a lovely friendship ur headline?"

Questions about Drake's propensity to text with teenagers arose last year when Brown talked about her relationship with Drake in a red-carpet interview at the Emmys. "I love him," she told Access Hollywood. "I met him in Australia, and he's honestly so fantastic… We just texted each other the other day and he was like, ‘I miss you so much,' and I was like, ‘I miss you more.' He's great."

She added that Drake has given her advice about "boys."

The public response to Brown's revelation that a 30-something man was texting her that he missed her was less than positive. But Drake did not respond to the controversy. Instead, then-14-year-old Brown defended the relationship on her Instagram story.


"Why u gotta make a lovely friendship ur headline?" she wrote. "U guys are weird … for real. I'm lucky to have people in the business extend their time to help me further my career and offer their wisdom and guidance. I'm very blessed to have amazing people in my life. U don't get to choose that for me. It's nice to have people who understand what I do. Now get back to talking about real problems in this world other than my friendships … jeez."

Then last month, another young performer revealed in an interview that Drake texts her, too. Billie Eilish, 17, told Vanity Fair, "Drake is like the nicest dude I've ever spoken to. I mean I've only like texted him, but he's so nice. Like, he does not need to be nice. You know what I mean? He's at a level of his life where he doesn't need to be nice, but he is. You know?"

I guess? Eilish's interview prompted more backlash against Drake on Twitter, but again, he did not comment.

Both Brown and Eilish referred to Drake as a kind of mentor, which is maybe fine. In the long history of Hollywood, there have been some older, male mentors with good intentions and some with catastrophically bad ones. What we know for sure: Drake frequently texts two very famous, underage girls, and that they think he is nice.

"I did not dine in DC recently"

Curiously, the tabloids have mostly ignored Brown and Eilish's comments about their relationships with Drake. In fact, in the same month that Brown talked about Drake at the Emmys, Page Six reported that Drake was dating a different teenager, albeit one who was 18.

In September of last year, Page Six claimed that Drake was dating Bella Harris, the 18-year-old model daughter of R&B producer Jimmy Jam. The gossip outlet cited a source who saw Drake and Harris having dinner at RPM Italian during one of Drake's tour stops in Washington, D.C. E! News confirmed the report, noting that Drake waited for the restaurant to "clear out" before sitting down at a table with Harris.


The tabloids then quickly noted that Drake and Harris first hung out backstage at one of his shows in 2016, when she was just 16. Harris posted photos from that night and from another show, in 2018, on her Instagram.

Drake, as is apparently his custom, did not comment on the report. But Harris denied that she went to dinner with him on Instagram, captioning a selfie with the following: "Coming off an amazing New York fashion week, I feel I need to set the record straight… I did not dine in DC recently. I was happily working & dining in NYC everyday."

She has not posted any photos of Drake since, and the story seems to have been abandoned.

The tabloids have also linked Drake to singer Jorja Smith, who appeared on his album More Life. In 2017, the Daily Mail reported that he was "secretly dating" Smith, who was 19 at the time. Drake declined to comment on the story. But fans have since speculated that his song "Jaded" on his 2018 album Scorpion—which includes the lyrics "We coulda waited, I wasn't rushin', difference in ages / You're old enough, but you're still a baby"—is about Smith.

"Act your age not your girl's age"

Given the limited information we have about Drake's relationships with Brown, Eilish, and Harris, and the fact that Drake has not publicly addressed any of the reports about them, it is hard to know what, exactly, he thinks about having relationships with teenagers. Is it appropriate to be friends with them? Text them? Date them?

One documented incident helps to shed some light on Drake's thinking.


Let's first discuss Drake's history with Kylie Jenner, 22. Recently, both People and Us Weekly have reported that Drake is romantically interested in Jenner, and that the two have been spending time together, though TMZ has refuted that it's anything romantic. But they have known each other for much longer. Remember when Drake had a feud with Jenner's ex-boyfriend Tyga?

A quick recap: In October 2014, Tyga told Vibe magazine that he thought Drake was fake. At the time, Tyga was rumored to be dating Jenner, who was only 17. So to get back at Tyga, Drake invited Jenner to his home for a party and posted a photo of her on Instagram with the caption "@kyliejenner in the cut." Then he released the song "6PM in New York" which called out Tyga directly: "It's so childish calling my name on the world stage/You need to act your age and not your girl's age."

The song forced Tyga to publicly deny that he was dating Jenner. (Jenner and Tyga went public with their relationship in August 2015, after she turned 18.) So from this incident, we can glean two things: One, Drake knows that it is, at a minimum, a "bad look" for an adult man to date a minor, and that calling attention to Tyga's relationship with Jenner was embarrassing for Tyga. And two, Drake thinks that it is okay for a 17-year-old Kylie Jenner to come to his house for a party.

Confused? Yes, me too. Unfortunately but unsurprisingly, a representative for Drake declined to comment on any of this.