Rapper Drake has to be one of the most charismatic presences in the hip-hop world at this point in time. Even his smile is contagious. The Canadian songwriter first popped up on people’s radar back in the 2000s when he appeared on the teen drama series Degrassi: The Next Generation, where he played the young Jimmy Brooks. He had actually taken the acting job as a means to help out his family, particularly his mother, who was sick at the time.
As we all know now, Drake (born Aubrey Drake Graham) left the show in order to pursue his rap career. He ended up dropping his debut studio album Thank Me Later in 2010. Since then, Drake has been a major success and has blown up over the past decade. He won his first Grammy in 2015 for Best Rap Album and has been a familiar face in both his home country and in the US.
Along with his music, Drake is also known for his complex love life. He has been on the arm of many beautiful women, who have long since proved themselves worthy muses in his world. A great deal of his art revolves around his love life and his love for women he deems high above him. But do can we separate fact from fiction when it comes to the women in his life? Here are 19 of some of the most amazing and stunning women Drake has ever courted.
19 Hopelessly Forever In The Friend Zone - Rihanna
Usually, when you think of Drake’s girls, the one that immediately comes to mind is the utterly flawless Rihanna (the couple has even earned the nickname “Hip Hop’s Ross and Rachel”). Their on-again, off-again relationship started back in 2009, which was the first time Rihanna concluded that she and Drake were simply “just friends” and attempted to cool the rumors that the two were dating. However, a few months later, Drake revealed that the two were “kind of” dating. His song “Fireworks” was even about his complex relationship with the hip-hop beauty and a short time later, she released her “What’s My Name” single featuring Drake (they played a couple in the video as well). Since then, they’ve always had a will-they or won’t-they vibe to all their collaborations and seem to drift back to each other when they’re not in relationships.
18 The One - Nicki Minaj
First, she was one of his closest friends and then, all of a sudden, they appeared to be bitter rivals. The story of Nicki Minaj and Drake has always been a complex one to put into words (much like it is with Rihanna). Drake has said in the past that he fell in love with Nicki the first time he laid eyes on her – that their relationship has always been a playful one. Back in 2010, he had commented that Nicki only saw him as a “little brother” of sorts while he was madly crushing on her. Their friendship drifted apart for a couple years and Nicki credited that to their busy and conflicting schedules – and, of course, his feud with her then-boyfriend Meek Mill. As we all know now, the hatchet has been buried and they’re back to being besties again.
17 Was It Just All A Game? - Jennifer Lopez
To fans, it was brief but memorable. To the rest of us, we were just sitting there with our heads spinning: Were Jennifer Lopez and Drake really an item? All of a sudden pictures of the two of them were appearing all over each other’s social media accounts. They seriously looked all cute when they were cuddled up with each other in numerous photos. However, a source close to the two told PEOPLE that their sudden pairing was “never very serious,” they remarked. “They like one another and had fun together.” The source went on to say that Lopez has a great deal of respect for Drake and his skill set. Lopez officially shot rumors down while visiting The Daily Show: “Let me clear this up. I’m not with Drake.” Later that month, it was revealed that Lopez was actually in a serious relationship with ex-MLB star Alex Rodriguez.
16 The Supposed Sister Fight - India Love
Most of us had never heard her name uttered until Drake became tangled up in a bizarre triangle with this Instagram beauty and… her sister? Drake had dated Instagram model and reality star India Love for a brief period of time before her sister Crystal happened to put their situation on blast for the world to see. Apparently, before India and Drake were an item, he was dating her sister Crystal, who then called out both of them. India had then wanted more of a commitment from Drake, which the young hip-hop artist wasn’t prepared to give at that point in his life (some believe he was still allegedly hung up on Rihanna and desperately attempting to get back in her good graces, which was one of the reasons why he broke it off with Love).
15 Just Friends? - Hailey Baldwin
We saw pictures of them EVERYWHERE. And, of course, when we see pictures of two celebrities stepping out in public together, we all like to automatically assume that they’re in a relationship – especially when the two people hanging out with each other are Drake and model Hailey Baldwin. At the time they were partying about the town, Baldwin had just gotten out of a relationship with pop star Justin Bieber. A source close to both told E! News that “nothing is going on romantically” between Drake and Baldwin and that Hailey was “still very much in love” with Bieber. Multiple sources came forward and said that the two were just really good friends. It’s a shame because they look extremely adorable in all their pictures together.
14 Sparks Flying - Amber Rose
Could it be just a crush? Amber Rose has dealt with her share of drama (especially when it comes to the Kardashian family and all the Twitter beef that went down thanks to Rose being Kanye West) but back in 2016, both she and Drake decided to ring in the new year with each other. She watched him perform in a crowd that included Casper Smart and Jennifer Lopez before joining him at his table with 2Chainz, Lil Wayne, and Birdman. Later, the two enjoyed a private dinner together at Prime 112. They had spent a few days together in order to bring in 2016 the right way. She even posted a video of the rapper dancing to Fetty Wap’s “Come My Way” and added heart-eye emojis in the caption.
13 Flirt On The Fritz - Zoe Kravitz
She is quickly becoming one of the most famous faces in Hollywood – and this time it’s not because of her uber-famous last name. Actress Zoe Kravitz happens to be the daughter of rock star legend Lenny Kravitz and actress Lisa Bonet (heck, her stepfather is even Jason Momoa – that’s one good looking family) so she really didn’t need any help to earn her rightful place in Hollywood – but she did thanks to her remarkable acting skills. A couple years ago, she was linked to Drake by the media back in 2013-14 thanks to them posting some cute pictures of each other on their social media accounts. Recently, the two were spotted again together at this year’s Golden Globes, so maybe it’s more serious than we all originally thought?
12 Pre Kardashian Drama - Blac Chyna
It seems that if you play the “six degrees of Kevin Bacon” using Drake, you could get to the Kardashian family in one simple move. Seems like, years back, Drake was actually a big fan of Blac Chyna (the mother of Rob Kardashian’s daughter and the ex of Kylie Jenner’s ex, Tyga – the father of Blac’s son). Drake even shouted out Blac in his 2010 song “Miss Me”: “Call the King of Diamonds and tell Chyna it’d be worth the flight”. Before the single dropped, people didn’t know that Drake and Blac were even connected. The piece actually boosted Blac’s star within the hip-hop world. Famously, both Tyga and Drake sported some major beef after Tyga called Drake “fake” during an interview. Hopefully, everything has cooled down between the rappers since.
11 Top Model Behavior - Tyra Banks
Tyra Banks is one of the definitive supermodels whose career blew up in the 1990’s. She was the first African-American woman to actually be featured on the covers of GQ magazine and the Sports Illustrated Swimsuit Issue. During her modeling days, she also gave a try at acting and starred opposite Will Smith in The Fresh of Bel-Air, and starred in films like Higher Learning and Coyote Ugly. In the 2000’s, she created her popular reality television show America’s Top Model and became a household name (as if she wasn’t already before). Apparently, the model briefly dated Drake after she starred in his music video for his single “Child’s Play”. In the video, she plays Drake’s girlfriend who picks a fight with him at The Cheesecake Factory. Of course, the rumors were denied by both parties.
10 The Beauty - Rita Ora
British singer and actress Rita Ora first hit the scene in 2012 when she was featured on DJ Fresh’s single “Hot Right Now”. Shortly afterward, she dropped her own debut album, which hit number one in the UK. Acting wise, the beauty famously played Christian Grey’s sister Mia in the movie adaptation of Fifty Shades of Grey and the film’s sequels. Drake actually penned Rita’s hit single “RIP”, after of which she joined him on tour and was his warm-up act. A short time later, because it’s Drake and he has a definite soft spot for beautiful women, it was rumored that the two were dating. If they were dating, it didn’t last very long since she was spotted kissing Diana Ross’ son Evan Ross at a party in a New York Club a short time after the rumors started.
9 Pure Infatuation - Serena Williams
It’s safe to say that almost everyone has been in love with the super talented tennis goddess Serena Williams during at least one point in their lives. Drake included. These days, Serena is busy juggling her personal life (after having a baby with her husband, Reddit co-founder Alexis Ohanian) and her tennis super start life (it should be noted that she was 8 weeks into carrying her daughter when she won the Australian Open in 2017). But back in 2011, Drake was all flutter when he would attend Serena’s tennis matches in order to cheer her own and stare at her lovingly. Some of his Tweets directed at her even suggested the two were dating. He became a regular at her matches in 2015 and they were spotted kissing at a restaurant in Cincinnati.
8 Age Is Just A Number - Taraji P. Henson
These days, actress Taraji P. Henson is ripping up both the small screen (playing Cookie Lyon on the hit Fox drama Empire) and the big screen (recently she starred in the thriller-drama Proud Mary), so her personal life is not exactly her number one concern at this point. But back in 2010, Henson was seen cuddling up with Drake in a downtown Vancouver restaurant (she was in Canada filming the Lifetime movie Taken From Me: The Tiffany Rubin Story at the time) and looking very much like a couple. However, when Henson appeared on The Wendy Williams Show, she quickly squashed rumors of them dating. She said that he was just a friend who liked her, but that their age difference got in the way (she said that he’s only seven years older than her own son).
7 Before Her "Bad Girls" Phase - Catya Washington
Most know Catya Washington as “Ms. Cat” from the reality show Bad Girls Club, but years back, she was actually a girlfriend of Drizzy. The two met on the set of the music video for “Best I Ever Had” and kept it casual at first, just tweeting at each other back and forth. Before long, she was having dinner with the rapper in Toronto after he flew her in. She said that it only took a month for them to go from friendship to dating. She eventually moved to Toronto to live with him (she even met his mother!). Eventually, it was Washington’s career that got in the middle of their relationship. She claimed that she wanted to go do the Bad Girls Club and he was against it, so they ended up parting ways.
6 Drake And His Models - Dollicia Bryan
Rumor has it that model Dollicia Bryan was actually the reason why Drake and Serena Williams never officially got together back in 2011 when he first started attending her tennis sets. Bryan and Drake met when his DJ at the time was DJ’ing her birthday party. They appeared to get even closer when they attended her SMOOTH magazine cover party. Bryan’s rep even confirmed that the two were an item: “Yes, Drake and Dollicia are dating. They’re both in L.A. right now spending the holidays together.” Shortly after it was revealed that the two were an item, Serena took to Twitter and went on a rant, cryptically saying that “you can do better”. Was she talking about Drake and Bryan’s relationship? Hum, fans wanted to know. Though, both he and Serena DID end up together a few years later, though.
5 "Best I Ever Had" - Sophia Marie
Sophia Marie is actually one of the models from Drake’s “Best I Ever Had” videos, another stunning model he was rumored to be dating. A source, who happened to be on the set of Drake’s “So Kodak” commercial shoot, and confirmed that he and the model were dating years back: “Drake’s got a new girlfriend that he’s keeping by his side at all times even when he works. Her name is Sophia Marie and I was on set when he was shooting for his new Kodak commercial and she was also in it. The director told me that he demanded she be a part of his video and he did not want to use the model that was chosen for him.” Drake even tweeted out a picture of Sophia on the set of the commercial.
4 Too Much Trouble - Shaye G
No relationship is without drama, especially when it comes to Drake and his relationships. Shaye G is an Internet model who was actually linked to Drake while he was reportedly in a relationship with Rihanna. TMZ reported that after the model posted some pictures of expensive purses that Drizzy bought her while they were together, the rapper sent her a slew of angry messages at her. They reported that the messages were so bad that Shaye’s father even got involved (and you know it’s bad when a girl goes to her father for protection). No one really understood why Drake was so upset with those specific pictures, but it’s clear that he managed to burn that relationship bridge with Shaye G after sending the angry messages.
3 No Lies Here - Deelishis
Yep, Drake had a relationship of sorts with former Flavor of Love reality star Deelishis. The model actually gained fame from the reality show when she won after Flavor Flav chose her over the other contestant, Tiffany ‘New York’ Pollard. Of course, THAT relationship didn’t last long and she stepped into modeling and some light acting in music videos. She models for Eye Candy modeling and appeared in music videos for Busta Rhymes and Paul Wall. She was even the lollipop girl in Lil Wayne’s “Lollipop” music video. Years later, Deelishis appeared in a cameo on the reality TV series Love & Hip Hop: Atlanta during the fifth-season finale. Deelishis often bragged about her relationship with Drake while he was in other relationships, which probably didn’t make his girlfriends happy at all. Yikes.
2 When On Vacation - Bernice Burgos
Not too long ago, Instagram model Bernice Burgos and Drake had a very cute relationship that they managed to keep out of the tabloid pages. Even though the relationship didn’t last long, the two are still on very good terms with each other. “Drake, I’m going to tell you something about Drake. He’s the sweetest person ever,” Burgos said during an interview with The Breakfast Club last year. “He’s always been good to me and I’ve always been good to him. I will go to his wedding right now if he gets married. He’s surely going to invite me. Why not? I’m cool.” She certainly would have to be in order to attend her ex’s hypothetical wedding. It certainly appears to be a rare thing in Hollywood to be on such good terms with your ex, so Burgos’ words are very refreshing.
1 Rumors Flying - Ravie Loso
After Drake’s romance with Serena Williams came to a sudden end, he became smitten with model Ravie Loso shortly afterward. Apparently, the couple went on a string of dates, one which included attending Kendall Jenner’s 20th birthday party back in 2015 (Drizzy if famously friends with Kim Kardashian’s hubby Kanye West, so OF COURSE he was invited to the birthday bash). Also in attendance at the party was Hailey Baldwin (also listed on here as one of Drake’s romances). Before the party, Loso would commonly meet up with Drake at The Nice Guy, a club in West Hollywood (though they would arrive separately and leave separately). People assumed that Loso was just a rebound for Drake after Serena, but they seemed pretty cute together during the short time they were dating.
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