Drake and his girlfriends: Who has he actually dated?

It’s been a busy week for Drake and his colourful love life after first getting accused of going on secret dates with Chris Brown’s ex-girlfriend Karrueche Tran and then allegedly trying to flirt with Diddy’s long-time love Cassie. Drama! They’re not the first high-profile ladies the How About Now rapper has been linked to over the years though as Drizzy seems to have tried his luck with most of showbiz, if reports are to be believed.

The 28-year-old hasn’t had an official girlfriend since bursting onto the hip hop scene in 2009 – as far as we know – but he hasn’t exactly been struggling to hook-up with beautiful women as his dating history tells us. There also seems to be some occasions where he’s been accused of gloating about dating his friends’ ex-girlfriends – giving a little weight to Chris Brown’s claims! So who exactly has Drake been linked to?


Drake's dating history: Tyra Banks

Drake’s dating history: Tyra Banks (WENN)

In 2012, Drake was seen enjoying a fun-filled day out to Disneyland with the America’s Next Top Model beauty, and he actually confirmed to Ellen DeGeneres that they briefly dated, telling the talk show host last year: “Jeez. I went on a date with her one time, just one date. We went to Disneyland in disguise, actually, which was fun. I don’t know if it was a date, it was a get-together. We’re close as well.”


Drake's dating history: Kat Dennings

Drake’s dating history: Kat Dennings (Brian To/WENN)

Confirming that they went on a date once, Drake told Ellen: “I just always had a huge crush on Kat Dennings, and she was kind enough one night to oblige me and we went out for dinner. They don’t call me back after one date, according to this. She’s great though.”


Drake's dating history: Nicki Minaj

Drake’s dating history: Nicki Minaj (Nicki Minaj/Instagram)

Rumours about the Young Money label mates secretly hooking up have circulated for years, but on Nicki’s recent track, Only, Drake denied having any sexual relationship with the curvaceous beauty although he admits he wouldn’t say no, rapping: “I never f****d Nicki, cause she got a man, but when that’s over, then I’m the first in line.”


Drake's dating history: Serena Williams

Drake’s dating history: Serena Williams (Alberto Reyes/WENN)

Remember when Drake and iconic rapper Common had a massive feud back in 2011? Well, according to Common, he admits that he was upset over rumours that Drake was dating tennis champ Serena, whom he had been in a serious relationship with for several years. Explaining the feud, Common said on the Rickey Smiley Morning Show in July: “Me and Serena was together. We broke up. I don’t know specifically her and Drake, it felt like obviously something was going on [after we broke up], I ain’t dwell on it too much. I ain’t have no problem with that, you do what you do. After a while I felt like in some of Drake’s songs he was saying stuff that was subliminal to me.”


Drake's dating history: Tika Sumpter

Drake’s dating history: Tika Sumpter (Ad Media/Splash News)

In an interview with Necole Bitchie in January, Get On Up actress Tika admitted that she and Drizzy had actually hooked up before he shot to fame. She revealed: “That was one date. The whole cast [of Nickelodeon’s Best Friend’s Date] went out to dinner. He was so nice. And I remember him being like, ‘I’m working on music,’ and he sent me some music, actually. So yeah, he’s been working on music for a long time. And I just remember- I used to call him Aubrey. And he was just super sweet and super nice.”


Drake's dating history: Rihanna

Drake’s dating history: Rihanna (WENN)

The world and her mother knows about Drake’s eternal infatuation with RiRi and she was actually the first high-profile lady he was linked to not long after he became a household name in hip hop five years ago. Their fling didn’t last long and they split but they found each other again in March this year. The on/off couple took their love affair to Europe as Drake performed on tour but once they returned to the US weeks later, it was over again. Admitting to the harsh reality of their romance, Drake told the New York Times: “You know what she was doing to me? She was doing exactly what I’ve done to so many women throughout my life, which is show them quality time, then disappear. I was like, ‘Wow, this feels terrible.’”


Drake's dating history: Cat Washington

Drake’s dating history: Cat Washington (Cat Washington/Instagram)

It sounds like Drizzy and the Bad Girls Club star were actually quite serious when they dated in 2009, as he wrote his hit single Best Song Ever about the model and she also told Necole Bitchie: “It was an awesome relationship. I was in love, he was in love and by the way in the song he said he was in love, so don’t try to switch it up now… It was good. I’m talking family dinners and we in Whole Foods pushing the cart around. It was a regular relationship. I was in love and he was in love but at the end of the day he started getting a little bit too loose. Meaning he pops up in the tabloids with Maliah, trips to Jamaica that I wasn’t invited to or never heard about.”


Drake's dating history: Maliah Michel

Drake’s dating history: Maliah Michel (Maliah Michel/Instagram)

Speaking of Maliah, Drizzy was linked to the curvaceous model in 2010 after she appeared in the music video for his video Find Your Love, and she revealed all the details on their relationship according to Fashion Style, saying: “Drake and I had a really great relationship sharing a really close bond. I don’t know if people really realised that…With Drake, he was always a gentleman, he was really sweet and he cared for me. He was great.”


Drake's dating history: Amber Rose

Drake’s dating history: Amber Rose (WENN)

In 2010, Drake was said to have been getting cosy with Wiz Khalifa’s estranged wife after she broke up with Kanye West, but Amber denied this on Twitter, telling her followers: “I was with my ex for 2 years and now I have a new love. If that makes me a Slore then so be it. I have NEVER slept with Fabolous, Drake, Chris Brown, Amare, Lebron, Cassidy etc. nor have I been a prostitute.”



In a rare confirmation of relationship status for Drake, a rep for the gorgeous model announced to the TheYBF.com that she and the Canadian rapper were officially a couple. Cute! They split soon after though and Drizzy was onto the next!

Will Drake ever find the right woman?