Want to Know About Drake Dating History? This List is For You

Are you curious about Drake dating history? The famous Canadian is behind some of the biggest hits ever. But he also has a pretty colorful past when it comes to girlfriends. It makes for quite the headlines now. But the most interesting thing is, he always kept it under the wraps. Many people have speculated about his romantic life now and then. But here is a list of the women he has dated to satisfy that itch meanwhile. Let us take a quick peek at it and find out more about Drake’s relationships. 

Keshia Chante

Did you ever want to know who “Kiki” is from Drake’s song “In My Feelings”? Well, it’s been revealed that singer and TV personality Keshia Chante is believed to be the famous “Kiki.” Although the exact year of their relationship is unknown, she is said to be Drake’s first teenage love.

During a 2013 episode of BET’s 106 & Park, Drake confessed to Keshia, saying, “You were one of my first crushes, and not many people know this, but I actually rapped about you before.” Some of his songs like Fallen, Deceiving, and Madonna have references to their past relationship. Surprisingly, these two exes remain friends to this day. Here’s a snapshot of them together in 2017!

Kat Dennings

Kat Dennings and Drake went on a date, but it didn’t develop into a serious relationship. They had dinner together, but soon after, Dennings received a lot of angry tweets from Drake’s fans. People were upset and sent messages like “f**k you, Kat Dennings” and claimed that Drake belonged to them. The situation became overwhelming for Dennings. Also, it appears this was an ill-fated relationship. Probably best for both that it ended before something serious. 

Jade Lee

Drake mentioned a woman named Jade Lee in his song “Karaoke” from 2010. They were both from Toronto and had a close relationship. In the song, Drake talks about wanting to marry her, but Jade felt that his lifestyle was overwhelming and decided to end the relationship.

SZA

Drake and SZA have been the subject of dating rumors for a long time. In his song “Mr. Right Now,” Drake mentioned dating SZA back in 2008. When asked about it in 2022, SZA confirmed that they did date and that they have always had a good relationship. She expressed her gratitude for Drake’s positive words about her and mentioned that it’s strange how things have changed over the years, with her now being an artist and Drake being a renowned figure in the industry.

Bria Myles

If you’ve ever wondered who inspired Drake’s song “Bria’s Interlude” from his 2009 album So Far Gone, it was none other than the beautiful Bria Myles. While Drake has never explicitly confirmed or denied their relationship, the fact that he dedicated an entire interlude to her suggests that they were involved.

In a 2017 interview, Bria admitted that she did date Drake. When asked about his performance in the bedroom, she laughed but chose not to answer.

Nebby

If Drake had one true love, it was probably Nebby, also known as Zineb Samir. We don’t have much information about their relationship, but it is confirmed that Nebby was one of Drake’s past loves. Also, he mentioned her in his song “Look What You’ve Done,” saying, “It’s like ’09 in your basement and I’m in love with Nebby / And I still love her but it fell through because I wasn’t ready.” It is also suggested that his song “Hotline Bling” was about her.

Rihanna

This love story truly touched our hearts! Drake openly expressed his love and admiration for the amazing Fenty Beauty mogul at the 2016 MTV VMAs. However, the Work singer found his confession ‘awkward’. She said they were not in a relationship anymore. Nevertheless, their chemistry is undeniable. Also, they looked really nice together. 

Catya Washington

After meeting on the set of his music video for “Best I Ever Had,” sparks flew between Drake and Catya, and they started dating a month later. Catya realized that Drake’s fame was growing when she saw him in tabloids with Malia and going on undisclosed trips to Jamaica. Despite being in love and having a regular relationship that involved family dinners and grocery shopping at Whole Foods, Catya felt excluded and noticed Drake’s behavior becoming more careless.

Maliah Michel

Maliah Michel appears in the video “Find Your Love.” Drake dated for quite some time after the release. We don’t know much about the details. But there was plenty of strain and tension between them. During Houston Appreciation Week, Drake publicly praised Maliah. She responded with a couple of tweets expressing her resentment. They exchanged plenty of ugly words and tried to take potshots at each other. 

Serena Williams

People saw Drake with Serena Williams many times from 2011-2015. He attended her matches. But Dake himself never acknowledged their relationship. Also, Serena made an appearance in Trey Songz’s music video “Bottom’s Up.” Then one fine day, we got to see both of them kissing in a restaurant. That was confirmation enough. 

Dollicia Bryan

In 2011, Drake and Dollicia had a short fling, and fans saw pictures of them together. However, their relationship didn’t last long, and they had a bad breakup over the topic of “colored contacts.” Dollicia didn’t like how Drake looked with hazel-colored contacts. Yeah, now that is a plain stupid reason to break up over. But I guess celebrities can get away with everything and anything. Also, full marks for excuses. 

Tyra Banks

During an appearance on The Ellen DeGeneres Show, Drake revealed that he dated supermodel Tyra Banks in 2013. They had a unique date at Disneyland where they disguised themselves. However, their relationship didn’t go beyond that one date. Tyra did make a cool cameo in Drake’s Child’s Play video, showing that they remain good friends. Also, just how long does this list go? At this point, all one can do is just wonder. 

Zoe Kravtiz

In 2013, this couple was spotted being affectionate at a Beyoncé concert and even shared pictures of each other on Instagram. The actress confirmed their relationship, describing Drake as “sweet” and a “cutie.” They were also seen together again at the Golden Globes in 2018. However, their relationship didn’t progress further, and Zoe joined the list of Drake’s ex-girlfriends. We wonder why. 

Blac Chyna

In 2014, there were rumors linking Drake to the controversial figure, Blac Chyna. This came about when Drake got into a Twitter feud with her then-boyfriend, Tyga, and claimed to have been intimate with her. Chyna further added to the drama by posting a suggestive picture and tagging Drake with a caption that hinted at their past.

After her breakup with Rob Kardashian, people spotted Chyna getting cozy with Drake on two separate occasions at clubs in Los Angeles. It seems like Chyna has shifted her attention from Tyga to another rapper!

Amber Rose

After his involvement with Blac Chyna, Drake was seen celebrating New Year’s Eve in 2015 with Amber Rose, who is a close friend of Chyna. However, both Drake and Amber have consistently denied having a romantic relationship. Who knows what it was? Only the partners can tell. 

Sophie Brussaux

Drake recently acknowledged his paternity of little Adonis, confirming that Sophie Brussaux is his baby mama. In his song “Emotionless,” Drake reveals that he had met Miss Brussaux only twice before she became pregnant. This relationship also did not last. And both of them moved on to greener pastures later in life. We have no idea what Sophie is doing at the moment. 

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