Reportedly the former "106 & Park" host dated Drake when she was 14.
The Canadians bonded over, well... maple syrup, being Canadian, and cold winters - Chante had just moved from Ottawa to Toronto to work on her music career and Drake, or "Aubrey Graham" as he was known back then, was starring on "Degrassi" before claiming his city as the "6 God".
Recording artist Drake and 106 & Park host Keshia Chante visits 106 & Park at 106 & Park Studio on September 23, 2013 in New York City.
WAY before she became our fit-spiration, blowing our minds in Kanye West's "FADE", Teyana Taylor was considered Drake's "#DayOne" BAE.
The rapper and Taylor have a LONG history (read: PRE or "pre-Rihanna era"). How long? Remember MySpace? Yeah, that long.
Teyana shared photos of her and Drizzy to her MySpace page way back in 2009, and the pair reunited for another cozy photo op in 2013.
"F**k all y'all n****s ...except my n****s ...meet the exception. #DayOne" @champagnepapi captioned the photo.
Since their alleged hook-up at a Lucky Strike in 2009, Drake and Rihanna's relationship reads like a complex romance novel.
For more details on their hook up, listen to Drake's track "Fireworks," and even though the rapper put his feelings on paper, Riri denied the relationship, claiming the pair were "just friends" during a radio interview.
Fast forward to 2010's "What's My Name," a loved-up mention in the Rick Ross track "Made Men" and a hot & heavy performance at the 2011 Grammys and romance rumours start swirling again.
But apparently their love was not made to last, although the couple got cozy on the track "Take Care," 2012 brought more Riri disses from her Canadian love.
2013 brought a cold mention about BadGalRiri from Drizzy during an appearance on Ellen. The rapper was asked to confirm relationship rumours with a bunch of ladies. His response to Rihanna's photo ""Yeah, great girl, we had our moment. Always support and have love for her." Cold.
Fans thought the pair had WORKed it out following the sizzling chemistry in two videos they put out for their track (not to mention one hot performance at the 2016 BRIT awards) and Drake seemingly confirmed our dream for the pair, proclaiming his love presenting Ri with the Michael Jackson Video Vanguard Award at the MTV Video Music Awards.
It only took a couple of months (and one shared shark tattoo) and the pair had split again, but we have a feeling this relationship still has some gas in the tank.
Who would say no to Drake, especially when he's taking you to Disneyland?!
Drake dished on his Disney date with Tyra Banks to Ellen, revealing "I went on a date with her one time yeah. We went to Disneyland in disguise actually, which was fun."
Ladies, we kind of get the idea that SOMETHING is going on when you call him Aubrey.
Case in point: Zoe Kravitz.
The actress has spoken out about her relationship with "Aubrey", saying the pair are "very good friends" but failed to explain the time they were seen sucking face at a Beyonce concert in 2013.
Most recently, Kravitz shared a photo of a smooch from Drake to celebrate his birthday and back in 2011, the rapper has called her "one of [his] favourite people in the world."
Yes, you heard that right. Drake dated "Two Broke Girls" actress Kat Dennings, lucky for Josh Groban, it was only dinner.
"I just had a huge crush on Kat Dennings and she was kind enough one night to oblige me and we went out for dinner," Drake told Ellen back in 2013.
The only person whose relationship with Drake might be more complicated than Rihanna's is Nicki Minaj.
Claiming more than once that the pair's relationship is totally platonic, Drake's lyrics seem to tell a different story.
From multiple marriage drops to claiming he's "first in line" after her relationship with Meek Mill is over to dissing her for not picking him in THAT feud, Drizzy's not one to mince words in his lyrics and we have a feeling there's more emotion behind these than the rapper's letting on.
Another complicated beauty that seemed to get overlooked by the rap world's most eligible bachelor, Serena Williams did reportedly get the seal of approval from Drake's mom.
The pair's relationship seemed to blossom while Drake was on the rebound from Rihanna, but that's definitely over considering Serena said "yes" to someone else.
From friends to something more?
Drake made more than a few appearances on Hailey Baldwin's Snapchat in the summer of 2016. The pair were first spotted getting cozy at Drake's Memorial Day bash and later Baldwin was spotted wearing HIS Toronto Raptors jacket.
But it seems that these two were never meant to be 'shipped, with Hailey's reps saying the pair are "just friends".
So yes, Jennifer Lopez has stated for the record that Drake "just asked me to do a song with him and that's what we've been doing," but is this how you'd pose with YOUR collaborator?
Okay, if it was Drake, maybe.
If they really are JUST COLLABORATING this must be one amazing track. The cuddly Instagram posts are one thing, but Drizzy showing up at your Vegas show, buying necklaces and throwing Prom-themed parties seem like the things a doting boyfriend would do and we couldn't think of someone more worthy of his attention than his "celebrity crush", JLo.