Canadian superstar Drake has definitely been rumored to have dated plenty of famous ladies over the years — and reality television star and makeup mogul Kylie Jenner is only the latest one. The 33-year-old rapper certainly dated his fair share of beautiful ladies and today our list is exactly about those. From singers such as Rihanna, Nicki Minaj, and Jennifer Lopez — whom you probably heard of getting cozy with the rapper — to names you might not expect to see on this list such as models Hailey Baldwin and Bella Hadid. While Drake may not have been too serious with a lot of the women on our list, he was certainly spotted with all these pretty ladies, which in the world of the rich and famous, usually means that something was going on!
Alright, now keep scrolling to see 20 famous women that rapper Drake has been connected to over the years!
20 Let's Start With Drake's Latest Girl, Kylie Jenner
According to Mirror, Drake is rumored to currently be dating reality television star and world's youngest self-made billionaire Kylie Jenner, after the two have been spotted spending more time together recently. Drake — who even performed at Kylie's 16th birthday party — has been a friend of the Kardashian/Jenner family for years now!
19 Who Could Forget About His Fling With Jennifer Lopez?
The 33-year-old rapper was also rumored to have been dating diva Jennifer Lopez, and we'd say that this photo is pretty solid proof of that. Drake, who is 33 years old, didn't seem to mind one bit that Jennifer is 17 years older, but honestly who would — the diva looks barely 30!
18 There Have Been Rumors About Drake And Rihanna's Relationship For Years
Drake and singer Rihanna, who collaborated on a few hits over the years — "What's My Name?", "Take Care" and "Work" only being some of them — have always been rumored to have had something going on. One thing is for sure — just friends or lovers, the two have always been pretty close!
17 He's Been Spotted Leaving A Club With Bella Hadid
Another famous face that Drake allegedly dated is model Bella Hadid. According to Elle, back in 2018 — while Bella and the Weeknd were on a break — Drake and Bella got pretty close and were even spotted leaving restaurants and bars together. It seems as if the model has a thing for successful Canadians!
16 Hailey Baldwin Is Another Model Drake Got Cozy With
And while Bella Hadid might have a certain type, it seems as if Drake has one as well as he has definitely been seen with quite a few successful models. In the pic above you can see him hugging Justin Bieber's wife Hailey Baldwin (before she and Justin were a thing, obviously).
15 And, Of Course, Nicki Minaj Also Made Our List
It is no secret that there have been rumors over the years of rappers Nicki Minaj and Drake dating — the two have collaborated on multiple occasions and they always seemed suspiciously close. While neither ever confirmed anything the two certainly seemed to be each other's biggest fans at one point!
14 Tyra Banks And Drake Allegedly Briefly Dated
While model Tyra Banks played Drake's love interest in his "Child's Play" music video, the two tried to be more than friends at one point. While on The Ellen DeGeneres Show back in 2013, Drake admitted that he took Tyra Banks out on a date and that certainly means something was going on.
13 He Seemed Pretty Happy With Actress, Zoë Kravitz
Even though Zoë Kravitz and Drake never confirmed that they were dating, in an interview for Complex Zoë did say that they were very flirtatious and that Drake is a "really awesome dude". Now, the two may have never gotten too serious, but something was definitely going on between them!
12 Drake Also Had A Thing With Singer, Rita Ora
While neither Drake nor singer Rita Ora ever confirmed anything, The Sun reported that the two were spotted kissing backstage at a concert — back in 2012. As you can tell from the pic above, the two definitely spent some time together so we would' be too surprised if they were more than just friends.
11 He Was Seen With Amber Rose On Multiple Occasions
According to Ranker, back in 2016 rapper Drake and model Amber Rose were spotted together at a New Year's Eve party, after which they've been seen going to dinner a couple of times. Neither one ever confirmed anything, but it's pretty safe to say they went out on a couple of dates.
10 Who Could Forget About Drake And Serena Williams PDA-ing In Public?
Rumors of Drake dating tennis star Serena Williams have started back in 2011, but it wasn't until 2015 that there were finally photos of the two together. Drake would support Serena at her tennis matches, and she would support him at award shows. Unfortunately, the two decided to split later that same year.
9 Drake Was Also Seen Leaving A Club With Blac Chyna
According to Ranker, back in 2014, Drake was kind of dropping hints that he is into model Blac Chyna — and she was not mad about it. Their fans were quick to notice that the two stars were actively liking each other's social media posts after which they have also been spotted leaving a club together.
8 There Were Some Rumors About Him And Jorja Smith
According to Daily Mail, Drake was secretly dating British singer Jorja Smith in 2017 and she was even featured on his album More Life. The two were spotted going shopping together, and that certainly seems like a couples activity. Now one thing is sure — Drake definitely seems to be into beautiful and successful ladies!
7 Drake And Taraji P. Henson Were Pretty Close
According to Ranker, in 2010 Drake and actress Taraji P. Henson seem to have been pretty close. As we already know from the fact that he dated Jennifer Lopez, Drake doesn't have a problem with dating a lady that's slightly older than him — Taraji was 40 at the time, while Drake was 24.
6 He Even Brought Rosalyn Gold-Onwude As His Date
In 2017 rapper Drake decided to bring NBC Sports Bay Area reporter Rosalyn Gold-Onwude to the NBA Awards which immediately sparked rumors of the two being a couple. Now while Drake bringing Rosalyn as a date to an award show doesn't necessarily mean they're dating, it's certainly quite likely they were.
5 Drake Briefly Dated Singer, Raye
The Sun writes that Drake also dated British pop singer, Raye last year. The two allegedly got close during their late-night studio sessions and ended up dating for a brief period. While there are no pics of the two out in public, there is this polaroid pic they shared on their social media.
4 He Told Ellen DeGeneres That He Took Kat Dennings On A Date
Another celeb that rapper Drake admitted to taking out on a date while he was a guest on The Ellen DeGeneres Show is actress Kat Dennings. And while the two stars ended up going only on one date, we figured that Kat Dennings still deserves a spot on this list.
3 Here's Drake Out And About With Model, Malakia Terry
Another pretty model that Drake was rumored to have been dating last year was Malakia Terry. According to Hollywood Life, the two were spotted out and about in Drake's hometown Toronto — and as you can tell from the photo above, they were totally fine with paparazzi taking photos of them.
2 He Was Also Dating 18-Year-Old Model, Bella Harris
According to The Sun, Drake was also dating 18-year-old model Bella Harris. The pretty lady signed a modeling contract with Elite New York City agency last year and she immediately caught Drake's eye. The two of them were seen getting cozy backstage at one of Drake's concerts, but it seems as if things never got too serious.
1 Lastly, Drake With His Baby Mama, Sophie Brussaux
To warp our list up, here's a pic of Drake and Sophie Brussaux having dinner together back in 2017. While the two seem to have been only a one-time thing, nine months later on Drake's birthday — October 24, 2018 — Sophie gave birth to a boy, and Drake eventually admitted that the boy was his son.
Sources: complex, elle, hollywoodlife, mirror, thesun