A Guide to Drake's Dating History, Including What Seems to Be a Budding New Romance

Contrary to popular belief, Drake hasn’t been in many relationships. While the artist loves love, he jokingly explained on The Ellen DeGeneres Show in 2013 that he goes on a lot of first dates. “They don’t call me back after one date!” he laughed, after confirming that the relationship rumours surrounding him and Tyra Banks were just that – rumours. The same goes for him and Kat Dennings: “We went out for dinner, but that was it.”

Of course, true Drake fans may not be surprised to learned this. He did, after all, spend close to a decade trying to woo Rihanna – TBT to the 2016 VMAs. Then, there was that one time in 2018 when Drake asked Heidi Klum out on a date and she ghosted him. “Sorry, Drake. You snooze, you lose. You know what I mean? He was basically like a week too late,” Klum told Ellen DeGeneres of her meeting her now-husband days before Drake reached out.

It’s been a few years since Drake has confirmed or even hinted that he’s in a serious relationship. However, the – apparently lavish – dates haven’t stopped. This month, Drake was spotted having a private dinner with model Johanna Leia in Dodgers Stadium. (The organisation confirmed to ABC7 that Drake made “a sizable donation” to the Los Angeles Dodgers Foundation in order to make the date happen.) Could this be the next chapter in Drake’s dating history? It’s too soon to say – so, for now, let’s take a look back at who else the rapper has been linked to over the years.

Getty / Kevin Mazur

Rihanna

Rihanna and Drake’s past is a complicated one to say the least. The two collaborated throughout the early 2010s, sparking rumours of an on-again, off-again romance. Drake told The New York Times that, just before he rose to fame, he felt like Rihanna played him like “a pawn,” by showing him quality time and then ghosting him. In 2013, Drake confirmed on The Ellen DeGeneres Show that they had shared a romantic “moment,” adding he’ll “always have love and support for her.”

By 2016, the pair had released their hit “Work,” performing together at several awards shows. Then, the 2016 VMAs happened. “Waiting through that speech was probably the most uncomfortable part,” Rihanna told Vogue about the presenter speech Drake gave, in which he infamously proclaimed his eternal love for her on national television. Two years later, Rihanna revealed that she and Drake weren’t friends, but they weren’t enemies either. “It is what it is,” she quipped. However, the two appear to be on good terms now.

Getty / Taylor Hill

Rosalyn Gold-Onwude

Although a relationship between NBA reporter Rosalyn Gold-Onwude and Drake was never confirmed, the two spent an awful lot of time together between 2015 and summer 2017. They continued to fuel romance rumours when they showed up smiling, hand-in-hand at the 2017 NBA Awards.

“The first thing was the connection because we’re both Black and Jewish,” Gold-Onwude told RESPECT at the time. She added that they originally met through mutual friends at a basketball game, and over time, began seeing more and more of each other. During the interview, however, she never referred to Drake as her boyfriend, only as a friend: “It’s been really cool to cultivate a friendship with him.”

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