Drake | Who Dated Who | Kylie Jenner, Rihanna, Sophie Brusseaux

Drake may be single at the moment and probably spending quarantine alone in his massive Toronto mansion, but over the years he has dated plenty of ladies. There's a ton of mystery surrounding his love life, and it's obvious he likes it that way. I mean it took us a while to even find out he had a son. If there was an award for having the most rumoured romances Drizzy would probably win. From his on and off relationship and love for Rihanna, even getting cozy with JLo, he's been linked to some of the most beautiful and powerful women in the industry. At the time of this recording, Drake is 33 years old and has amassed a ton of success in his music career and more. Of course he's a catch and knows this, so it's no wonder plenty of ladies would love the chance to get to know him. One thing's for sure, Drake hasn't met the lady of his dreams just yet, and it wasn't kiki either. But his list of lovers isn't exactly short. There's his baby mama Sophie who you probably know about, but who would have guessed he hooked up with the now married Hailey Bieber. In this video I've got everyone from Drake's celebrity dates, to his flings, and even his first girlfriend ever. What's going on guys, it's Kara back at it with a series we've titled Who Dated Who, and today I'm going to give you the rundown of Drake's dating history. These videos might get intertwined because a lot of these celebs are connected by hookups. We recently did one on Kylie Jenner which we'll link at the end, and who knows, she may even appear on this list too. As we do with our other series, I need you guys to let me know who to do next in the comments down below. How about some other famous dudes? You let me know, you know where, and I'll see you guys after the intro. Let's rewind back to 2000 and Drake's first girlfriend. This is the famous kiki that Drake has brought up if you didn't know. Keisha Chante is a Canadian singer, actor and more. I actually loved her songs when I was a kid. Two grew up in Toronto together, and dated in their teenage years from 2000 to 2002, which makes sense because they were both in the industry. When Keisha interviewed Drake back in 2013, he told her, you were one of my first crushes and a lot of people might not know this but I actually rapped about you before. And not only when he refers to her nickname Kiki. On his mixtape from 09, Born Successful, Jersey discusses his relationships with her on a remix of her song Fallen. He also dedicated his 2015 song Madonna to her. But Keisha also said that she wouldn't accept the title of girlfriend cause they were so young. What do you guys think? It only makes sense that Drake was linked to fellow Young Money rapper Nicki Minaj. The two were super close in 2009 and 2010, and there were constant rumours of them being more than just friends. Drake proclaimed he had a crush on her and wanted to marry her on his Take Care album, and then there was the laugh dance in Nicki's Anaconda video. Talk about chemistry. Despite all that, Drake and Nicki insist they're like family to each other. In 2010, Drake was said to be dating another Hollywood lady, this time actress Taraji P Henson. She's 49 at the moment so there's a bit of an age difference, but Drake has admitted he likes older ladies too because of the experience, maturity, and the conversation. Drake denied the rumours they were dating even though they allegedly spent the 4th of July together in Toronto. Later Taraji told Wendy Williams, Drake was a friend. It was cute because I knew he liked me and I kept looking at him like if you were 10 years older, boy woo, but no I couldn't because he is 7 years older than my son. Another rumoured fling that followed Drake for some time was about him and tennis superstar Serena Williams. He was spotted watching her matches on a number of occasions from 2011 to 2015, and even though the two never confirmed the relationship, I'm pretty sure they were caught. Not only did the video of them making out on a dinner date in Cincinnati surface, there were the flirty tweets Drake sent her, and he even referenced Serena on a few of his songs like Worst Behavior. Let's not forget his beef with Common, Serena's ex. In an interview with Ellen, Drake chatted about some dates he'd been on in 2013 that may surprise you. First, there was actress Kat Dennings. He said, 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. And then there was supermodel Tyra Banks who Drake took to Disneyland explaining, it was just one date. We went to Disney in disguise actually which was fun. Tyra would also appear in his Child's Play video and they remained friends. Unfortunately these dates were just a one time thing and it seems nothing came of either. Drake would also be linked to stars like Rita Ora and Zoey Kravitz. In fact, Zoey may have been the real deal for a moment cause she later confirmed it. Also calling Drake sweet and a cutie. The hot couple was seen canoodling at a Beyonce concert in 2013 and appeared in each other's Instagram pics since. They were also seen later in 2018 flirting at the Golden Globes too. This next one you all know. Drake's love for Rihanna was certainly no secret, and if it was, he did a lousy job hiding it. I didn't know where to put this one on the list since their relationship seemed to be on and off for years. Since around 2009-2013 or something like that. The pair was spotted on dates, bowling together at Lucky Strike in New York, and making out and leaving clubs together on a handful of occasions. Drake has written lyrics about RiRi and would later confess his love for her at the 2016 VMAs. But sadly, RiRi found his confession awkward and claimed they no longer had a relationship. It seemed that maybe Drake was the one who felt a little harder. Still, the pair had undeniable chemistry, which we've seen in songs like Take Care and What's My Name. Sources say that these days the two don't have a friendship anymore. What a shame. Fast forward to 2016, a year that brought some new hookups for Drake. I had no idea that Drake was linked to Hailey Bieber. Back then she was still Hailey Baldwin, but she reportedly already had her eye on her now hubby, so maybe that's why nothing happened with Drake. The two were hanging out on Memorial Day weekend, but nothing more ever came of it. Later in December of the same year, Drake shocked us all when he got cozy with Jennifer Lopez. I, for one, didn't expect that. Not to mention they posted this photo cuddling on Instagram for the world to see. JLo supported Drake at his New Year's show in Vegas, and clearly this pic confirmed the pair's whirlwind romance. Clearly Drake didn't lock her down for long, but the fling was iconic enough to go down in pop culture history. Shortly after JLo, in early 2017, Drake would meet former adult film star and artist Sophie Brissot. I wonder if he knew this French bombshell would end up being the father of his child. They were first spotted together in Amsterdam having dinner with a group of friends in January, but it was a super secret relationship to say the least. In May of the same year, Sophie went public with claims she was in fact pregnant with Drake's baby. It wasn't until almost a year after their son Adonis was born that Drake went public about it. He confirmed on his Scorpion album that he is indeed the father, and according to his lyrics on Emotionless, he and Sophie only hung out twice but it was enough for her to get knocked up. These days, Sophie's currently found a job in Toronto which allows Drake to be closer to his son. And it's a job as an artist, not an adult film star, just to clarify that. Another lady Drake referred to on the Scorpion album was none other than supermodel Bella Hadid. Despite her on and off again relationship with fellow Toronto musician The Weeknd dominating headlines, she was briefly linked to Drake too. His lyrics about her read, fashion week's more your thing than mine, and you stay on my mind, you and your sister too hot to handle. Rumors circulated that the rapper pursued Bella for 4 months, whining and dining her, and even threw her a 21st birthday party. Apparently Drake then ignored her via text. Bella wasn't a fan of these rumors and took to Twitter to confirm nothing happened. But I'm not sure I believe her. One of Drake's love interests was the Jamaican-Irish Instagram model Malaika Terry. I mean he's been linked to a few insta models, but this one stood out. In 2018 they were an item and pictured holding hands in Toronto, while going on a series of hot dates, and Malaika was also using his lyrics as captions on her pics. Not to mention, sources say she even got to meet Drake's mom. Bella Hadid was not the only Bella that Drake allegedly dated. In 2018 it was said he was in a relationship with a much younger model, Bella B Harris who was only 18 at the time. This one caused some controversy as certain tabloids said he in fact met her when she was only 16. But her family is connected in Hollywood so it kinda makes sense. Despite rumors that Drake shut down an entire resto in DC for them to go on a date, the pair denied that they dated. There's another weird connection here too, Bella actually worked with Drake's ex Rihanna before as well. This next hook up may be Drake's most controversial. The rapper was linked with none other than Kylie Jenner at the end of last year when it was rumoured they were flirting at his birthday party. They seemed to be enjoying each other's company, they were joking around, and Kylie was laughing. She seemed to be really happy and in a great mood, and her and Drake seemed very comfortable with each other. There seemed to be an attraction there. That's what a source said about their relationship, but nothing came of this. And as you and I both know, Kylie is still on and off again with Travis Scott. More recently, it seems Drake was enjoying a romance with model Iman Hamam during New York Fashion Week in February 2020. They were filmed cozying up, enjoying some intimate chats, and getting touchy with one another. However, nothing about their relationship blossomed since. Well, that about wraps it up for our list of who Drake has dated, and as of March 2020, apparently the man is single and on the market. Drake comes across as a bachelor type, but from this list we can see he's actually dated a ton of ladies, he just hasn't settled down. Clearly there are even more IG models and famous women that the rapper's been linked to, but that would have been way too many hook ups to go through. Hopefully some of the mysteries surrounding Drake's love life as well demystified for you guys after watching this video. I guess we'll just have to see if Drake ends up finding the lucky lady who will change his status. Until then, we can look forward to some more hit songs and lyrics he writes about the ones that got away. Of course I want to hear from you guys in those comments down below. Did you know about all of Drake's flings on this list? Were there any I left out? If you like these who dated who videos, let me know whose list you'd like to see next. Make sure you're subscribed and follow me on Instagram if you want to chat more. If you like these who dated who videos, let me know whose list you'd like to see next. Make sure you're subscribed and follow me on Instagram if you want to chat more. I'll see you next time with some new videos. Bye!