Drake isn’t only famous for his quotable lyrics but also his on-and-off again relationships with the likes of Rihanna and supposedly, the bootylicious Jennifer Lopez.
Unlike his music, his love life is kept under-wraps with little information being leaked about his girlfriends, leaving the rest of us eager to know more, like who is Kiki? And does she really love Drake? One thing’s for sure, Drizzy hasn’t met the lady of his dreams just yet.
From famous faces like Bella Hadid to unknown Instagram models like Zmeena, here’s a list of Drake’s dating history and timeline of his relationships so far…
Ex: Keshia Chanté
Who is She? Singer & TV personality
Dated In: 2000’s
Ever wanted to put a face to the mysterious “Kiki” from In My Feelings? Well, here you have it. Indeed, singer and TV personality Keshia Chante is said to be the famous “Kiki” from Drake’s famous lyrics. We don’t know what year they actually dated, but she is apparently Drake’s first teenage love.
On a 2013 episode of BET’s 106 & Park 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.” Songs that have referenced his puppy love include Fallen, Deceiving and Madonna. Turns out these two exes are still buddies! Here’s a snap of them back in 2017!
Rumored Ex: Tika Sumpter
Who is She? Actress
Dated In: 2005
We can’t guarantee this actress was actually one of Drake’s lady loves, but it’s common knowledge that they went out to dinner and she definitely had a crush on him. Drizzy and Tika Sumpter potentially had a fling during his days on DeGrassi: The Next Generation.
She once revealed, “I have a slight crush on Drake. I’ve known him for a really long time… He was our celebrity set-up, so we set him up on dates and we had dinner. He’s such a sweet person. I haven’t seen him in a really long time. He was genuinely a sweet guy.”
Ex: Kat Dennings
Who is She? Actress
Dated In: 2005
Okay, we can’t really call this one an “ex” per se, but it is official that she went on a date with Drake. Things could have gone further, but it seems Kat Dennings found the relationship too overwhelming. After having sushi dinner together, Dennings said that she was swarmed with a lot of angry tweets from Drake’s fans. She said, “I looked at some of the @’s and they were like ‘f**k you, Kate Dennings,’ like, ‘you can’t Drake from me, he’s mine.”
Drake also confirmed on The Ellen DeGeneres Show that he did indeed go on a date with Dennings, saying he’d “always had a thing for her.”
Ex: Jade Lee
Who is She? Event planner
Dated In: 2006
Alexa play Karaoke by Drake. You may recall Drake rapping about a “wedding planner” he wanted to wife up during the 2010 track. Well, this lady was very much one of his first loves, Jade Lee. The two grew up in Toronto and clearly, she was wifey-material. But according to the lyrics of the song, Jade realized Drake’s life was “too much” and thus sadly ended things.
Ex: SZA
Who is She? Singer
Dated In: 2009
There has been speculation for years now about whether Drake and SZA ever dated. Well, after hinting about an old romance in his Mr. Right Now lyrics, SZA has finally come forward to tell the world that, yep, she once dated “King Drake”.
Drake’s Mr. Right Now lyrics included the line, “Said she wanna fu*k to some SZA, wait/’Cause I used to date SZA back in ’08.” In 2022, when asked about this line, SZA told Audacy:
“In a strange way, I was like, ‘Did they know?’ But they didn’t ask me to be in it. Nobody said anything…We’re cool, we’ve always been cool. It’s never been weird. It’s never come completely out of the blue,. Anytime he’s ever mentioned me, it’s always been positive. He’s never said anything negative about me. I’m grateful for that and I think highly of him, and I think it’s really weird that as all these years went past, I am an artist now and I wasn’t then and he’s King Drake.”
She later confirmed in a tweet that they actually dated in 2009, not 2008.
Ex: Bria Myles
Who is She? Actress & Model
Dated In: 2009
If you’ve ever wondered who Bria’s Interlude from Drake’s 2009 album So Far Gone was inspired by, look no further than this stunner. Drake has never confirmed or denied a relationship with actress/model Bria Myles, but having a whole interlude titled with her name pretty much tells us he did.
In a 2017 interview, Bria confirmed that she did date Drake and when asked if he was good in bed, she laughed, but refused to give an answer.
Ex: Nebby
Who is She? Unknown
Dated In: 2009
If Drake had one true love, it was probably Nebby, AKA Zineb Samir. Not much is known about this particular love interest, but we can confirm that she was indeed one of Drizzy’s former loves. Nebby has been referenced in his track, Look What You’ve Done with the line, “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’s also suggested that Hotline Bling was about this young lady.
Ex: Rihanna
Who is She? Singer
Dated In: 2009 – 2016 (on & off)
Here’s a love story that really touched our hearts! Especially after Drake confessed his love and admiration for the Fenty Beauty mogul at the 2016 MTV VMAs. Sadly, the Work singer found his confession ‘awkward’ and confirmed that they no longer had a relationship. Despite this, the duo’s chemistry is undeniable.
Drake has written lyrics about Rihanna and even gotten up, close, and personal with her in music videos, but the musicians have never actually admitted to ever having a romance. We’ll ship this couple till the day we die…
Rumored Ex: Teyana Taylor
Who is She? Singer
Dated In: 2009 & 2013
This superstar was rumored to have hooked up with Drake not once, but twice! First, in 2009 when Teyana posted a photo of the two almost kissing, which she later attributed to being “besties”; and again in 2013 when Drake shared a snap of him cuddling the Concrete singer. Nothing more ever came out of this hook-up, leaving it all to fans imagination.
Ex: Catya Washington
Who is She? Model
Dated In: 2009-2010
After meeting on the set of his Best I Ever Had video, sparks began to fly between Drake and Catya, before officially dating a month later. It seems these two were the real deal until Cat realized the rapper was making a name for himself.
She revealed to Hot 107.9 that they were indeed “in love” – “I was in love. He was in love. I’m talkin’ family dinners, we in Whole Foods pushing the cart around, it was a regular relationship. But he started getting a little bit too loose. He pops up in tabloids…with Malia. Trips to Jamaica that I wasn’t invited to and never heard about.”
Ex: Maliah Michel
Who is She? Exotic dancer
Dated In: 2010
You may recognize Maliah Michael from Drizzy’s Find Your Love video. Well, turns out these two had a short fling that same year the clip was released. We don’t know much about this affair, but we do know the two currently have bad blood.
When Drake “retired her jersey” during Houston Appreciation Week, the dancer retaliated with a bunch of tweets saying, “Y’all don’t know that ni**a been trying to make me stop dancing. Always putting me down about it….Always telling me I’m not better than anyone else in the club selling a** instead of dancing. But ni**a can’t stay out the club…”
Rumored Ex: Taraji P. Henson
Who is She? Actress
Dated In: 2010
In late 2010, it was rumored that the famous rapper had his eyes set on a cougar, also known as Empire actress, Taraji P. Henson. She later confirmed that they were just friends but if he’d been 10 years older, she would have definitely been down for some dating.
We guess this one just wasn’t part of God’s Plan…
Rumored Ex: Nicki Minaj
Who is She? Rapper
Dated In: 2009 – 2010
It only makes sense that these two rap-stars were super close as they’re both signed to Lil Wayne’s Young Money label. But we’ve always felt like there’s been something more between them than just friends.
From Drake proclaiming that he had a crush on her and wanting to marry the rap queen on his Take Care album, to lap dancing in Nicki’s Anaconda video, the chemistry between these two rappers has never been clearer. Unfortunately for Nicki and Drake shippers, the two continue to insist that they’re simply “like family” to each other.
Ex: Serena Williams
Who is She? Tennis Player
Dated In: 2011 & 2015
Drake was spotted a number of times watching Serena Williams play tennis throughout 2011 to 2015 but never confirmed that they were dating. She also appeared in Trey’s Songz’ Bottom’s Up video, which was reportedly shot in Drake’s condo. Then photos surfaced of the duo kissing in a restaurant, pretty much confirming their hook-up.
It’s safe to say that this relationship will never rekindle though as the tennis superstar is now married to Reddit founder, Alexis Ohanian.
Ex: Dollicia Bryan
Who is She? Actress
Dated In: 2011
Drake and Dollicia shared a brief fling in 2011, with photos of the pair together circulating among fans. Not much came out of this hook-up, except a bad breakup over “colored contacts”. Apparently, Dollicia “didn’t think hazel-colored contacts were a good look” on the rapper. OKAY…
Rumored Ex: Rita Ora
Who is She? Singer
Dated In: 2012
After Drake wrote Rita’s single R.I.P. in 2012, there were rumors flying that the British bombshell and Canadian rapper were an item. She also appeared in Drizzy’s video for The Feeling of Pain, which confirmed their undeniable fondness for each other.
Whether Rita was Drake’s girlfriend or not, we think these two would have made a super cute couple, don’t you?!
Rumored Ex: Cyn Santana
Who is She? Model
Dated In: 2013
Yet another lady in his slew of exes includes Cyn Santana, model and star of Love & Hip Hop. Drake met Cyn on the set of the No Lie video clip and were allegedly spotted together a few months thereafter. We don’t have much more on this fling, but we have found out that Drake’s song Company may well be about the gorgeous model.
Rumored Ex: Tatyana Ali
Who is She? Actress
Dated In: 2013
Rumors of a romance between Drake and the Fresh Prince actress were rampant in 2013 after he surprised her with champagne and PDA for her birthday. Drizzy even rapped on his song Tuscan Leather, “The Fresh Prince / just had dinner with Tatyana, no lie / all these ’90s fantasies on my mind / the difference is that with mine / they all come true in due time.”
Despite the saucy lyrics, Tatyana denied any involvement with Drake on The Real, saying they never hooked up.
Ex: Tyra Banks
Who is She? Top Model
Dated In: 2013
The lyrical legend confirmed on The Ellen DeGeneres Show that he dated supermodel, Tyra Banks in 2013. And, it wasn’t just any old date – the pair went to Disneyland in disguise! How fun!
Sadly, it was a one-time thing and the relationship ended before it even started. She did make a super-cool cameo in his Child’s Play video, though, confirming that the two remain good friends.
Ex: Zoe Kravitz
Who is She? Actress
Dated In: 2013 – 2014
This hot couple were caught canoodling at a Beyoncé concert in 2013 and have even appeared in each other’s Instagram pics since then. The actress confirmed that she and Drake were indeed an item, and that Drizzy was “sweet” and a “cutie”. But it doesn’t end there – the pair were seen rekindling an old flame at the Golden Globes in 2018, too!
Eventually, Zoe became just another of Drake’s ex-girlfriends as nothing new came out of this fling.
Ex: Blac Chyna
Who is She? Model & Entrepreneur
Dated In: 2014 & 2018
Drake was originally linked to bad girl, Blac Chyna in 2014, when he publicly got into a Twitter spat with her then-boyfriend Tyga, claiming that he “smashed her”. Chyna then added fuel to the fire by uploading a provocative picture, which she tagged Drake in, with the caption “Miss Me……#neverforget”.
Following her fall out with ex, Rob Kardashian, the model has been seen on two separate occasions cozying up with Drake in L.A. clubs. Forget Tyga, it seems like Chyna’s getting her claws onto another rapper!
Rumored Ex: Bernice Burgos
Who is She? Model
Dated In: 2015
When Drake and Bernice were photographed kissing in Australia back in 2015, people were certain that the model was the leading lady in his life. Despite the dating rumors though, Bernice clarified later in 2017 that the duo were merely “just friends”.
Rumored Ex: Amber Rose
Who is She? Model
Dated In: 2016
After his fling with Blac Chyna, Drizzy may have moved on to her BFF. The controversial Amber Rose was spotted partying with Drake on New Year’s Eve in 2015 but they have both denied a romance ever since.
We wouldn’t put it past them to casually hook-up, but it’s clear that their relationship would never go further than that!
Rumored Ex: Hailey Baldwin
Who is She? Model
Dated In: 2016
Justin Bieber’s wife was linked to the Scorpion rapper after they hung out during Memorial Day weekend in 2016. Entertainment Tonight reported that the pair were “totally engrossed in conversation” and couldn’t stop “smiling” at each other during the meal.
But it seems like the two were just friends, as the supermodel had her heart set on her current man, even back then! We’re so glad she found her fairy-tale ending.
Rumored Ex: India Love
Who is She? Instagram Model
Dated In: 2016
Drake shared a short affair with Instagram model, India Love back in 2016 amidst his on-and-off relationship with Rihanna. Funnily enough, India’s ex-boyfriend, Cliff Dixon, was rumored to have cheated on her with Rihanna. What a love triangle!
Drake later confirmed that this fling was nothing serious and that the socialite was just doing it to get a larger following on social media.
Rumored Ex: Jennifer Lopez
Who is She? Singer & Actress
Dated In: 2016
J.Lo’s boyfriend list goes on and on, but one that got the people talking was this reported fling! The Dinero star supported Drake at his Vegas show for New Year’s and sorta confirmed their rumored romance by sharing a post on her own Insta page.
Whether the relationship was the real deal or not, we’ll never know, but Drake did rap in Diplomatic Immunity in 2017, “I lost a J. Lo”. She clearly wasn’t Drake’s girlfriend for too long, but this rumored iconic fling will certainly go down in pop culture history…
Ex: Sophie Brussaux
Who is She? Former Adult Film Star
Dated In: 2017
Drake’s baby mamma, Sophie Brussaux has been in the public eye a lot lately, after Drake confirmed on his Scorpion album that he is indeed the father of little Adonis.
According to the rapper’s lyrics on his track Emotionless, the pair had only met twice, but that was enough to get Miss Brussaux knocked up.
Rumored Ex: Jorja Smith
Who is She? Singer
Dated In: 2017
The pair collaborated in 2017 when Jorja opened his Boy Meets World tour in Birmingham. During this time, it was rumored that the singer was his girlfriend and that his tattoo of the number ‘11’ was dedicated to her birthday – June 11th.
Fans added more fuel to the fire when they took to Twitter to speculate whether Drizzy’s song, Jaded was actually about Jorja…
Rumored Ex: Rosalyn Gold-Onwude
Who is She? NBA Sports Broadcaster
Dated In: 2017
This lucky lady was the only other woman apart from Drake’s mother to walk a red carpet with the Canadian star. The pair looked super cute posing together for the paps and at the time, a source told E Online that “He likes how normal she is, and she has her head on straight. They laugh and are enjoying getting to know each other.”
It was later reported that they were just close friends.
Rumored Ex: Bella Hadid
Who is She? Model
Dated In: 2017
Another star that Drake’s Scorpion album refers to is top model, Bella Hadid who has also been linked to The Weeknd. Rumors circulated that the rapper pursued Bella for four months, wined and dined her, and even threw her a surprise 21st birthday party, before allegedly ignoring her by text!
Bella took to Twitter after the release of the album to confirm that nothing happened – although we’re not sure we believe her…
Rumored Ex: Raye
Who is She? Singer
Dated In: 2018
Drake was spotted in London with Decline singer Raye following dating rumors earlier in 2018. It was reported that the hip-hop star took an interest in the singer’s songwriting skills and hung out with her quite a bit whilst working in the U.K.
Whether they were romantically connected or not, this music duo got to know each other over a string of dates in London town and hey, they did indeed make a cute couple.
Rumored Ex: Malaika Terry
Who is She? Instagram Model
Dated In: 2018
One of Drake’s love interests was the stunning bikini model, Malaika Terry. The pair were pictured holding hands in Toronto, while going on a series of hot dates. There was no information on how long they’d been an item, but the Jamaican-Irish model was using Drake’s lyrics as captions on her popular Instagram account.
Malaika later confirmed on the Rickey Smiley Morning Show that they were just good friends.
Rumored Ex: Zmeena
Who is She? Actress & IG Model
Dated In: 2018
Around the same time that Drake was spotted holding hands with Malaika Terry, he was also seen leaving a restaurant with Instagram model, Zmeena. We’re not sure whether he’s set his sights on this curvaceous celeb or whether this was just another one of his attempts at dating.
One thing’s for sure, the twerking Zmeena has received a backlash of nasty comments after her pictures appeared with the Scorpion rapper.
Rumored Ex: Kim Kardashian
Who is She? Reality TV Star
Dated In: 2018
This apparent affair got the whole world talking – and singing! Drake’s In My Feelings lyrics (“Kiki, do you love me?”) had people assuming he and reality TV star, Kim Kardashian had a secret relationship.
Fuel was added to the fire when Drake feuded with Kanye West, making everyone think he’d hooked up with Ye’s (then) wife as payback. Kim was quick to debunk the rumors though with a tweet saying, “Never happened. End of story.”
We enjoyed the tea while it lasted…Then the tea-cup filled up even more!
Drake released his single Search & Rescue, which sampled Kim speaking on E! about her divorce with Ye. The cover artwork for the single also featured a Kim-lookalike, reminiscent of a photo Kim had recently posted.
Rumored Ex: Stefflon Don
Who is She? Rapper
Dated In: 2018
Rumor has it that Drake was dating British rap star, Stefflon Don. After exchanging flirty messages during Drizzy’s Instagram Live session, the duo were spotted getting cozy at dinner in Miami back in November 2018.
“I’m a confident guy, I hold my own in any room, I’ve known you for a while, we buss ’nuff jokes together,” he told the artist during their cheeky Insta convo. Drake, Stefflon, we’ll have our eyes on you!
Rumored Ex: Kylie Jenner
Who is She? Reality TV star
Dated In: 2019
Drake has been linked with a fair share of famous gals, but this apparent hook-up might be his most controversial! The rapper was linked with Kylie Jenner at the end of 2019 when it was rumored they were flirting at his birthday party.
A source told US Weekly, “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.” Nothing seemed to come out of this rumor though, putting dating speculations to rest.
Rumored Ex: Julia Fox
Who is She? Actress
Dated In: 2020
While it’s yet to be confirmed, rumor has it that Drizzy also hooked up with Kanye West’s ex-girlfriend, Julia Fox. The pair apparently got together in February 2020, according to Page Six.
This “secret romance” started when Drake reached out to the Uncut Gems star via Instagram DM. They ended up going out for drinks and he even gifted her with two Birkin bags on Valentine’s Day. We bet Ye isn’t happy about that…
Rumored Ex: Imaan Hammam
Who is She? Model
Dated In: 2020
Drizzy was linked to another gorgeous model early 2020 when he was videoed cozying up with Imaan Hammam during New York Fashion Week.
The footage showed the duo enjoying an intimate chat and getting touchy feely with each other, but nothing about their relationship has blossomed since then…
Rumored Ex: Naomi Sharon
Who is She? Singer-songwriter
Dated In: 2021
Drake was dubbed a “home-wrecker” in the summer of 2021 when he allegedly broke up singer Naomi Sharon’s eight-year relationship and engagement to her (ex) fiancé, Jamie Sun. According to Jamie, Naomi signed a record deal with a “world star” (a.k.a. Drake), only to discover that his “trust” was broken, alluding to a possible affair between the two.
Naomi was also reportedly spotted in the gym with Drizzy, while he was caught liking raunchy pictures of her on Instagram. But that’s all we ever heard of this sneaky affair!
Rumored Ex: Johanna Leia
Who is She? Model
Dated In: 2021
After meeting through their mutual love of basketball, a romance between Drake and Johanna reportedly heated up during the fall of 2021. After attending a basketball game together, rumors swirled that Drizzy took Johanna on an extravagant private date by renting the Dodger Stadium in Los Angeles just for her.
Although he shared a cute photo of them together on Instagram, Drake and Johanna supposedly split just a month later.
Rumored Ex: Chantel Everett
Who is She? 90 Day Fiancé star
Dated In: 2022
After 90 Day Fiancé star Chantel Everett split from her husband of six-years, Drake was quick to take a chance at having a potential fling with her. Rumor has it that the Certified Lover Boy pursued the TV star by sending her DMs “to see how she was doing and where her head was at.” Although a source claimed that their relationship was in the “early stages”, nothing more ever came about.
Rumored Ex: Cecilia Rose
Who is She? Tik-Tok star
Dated In: 2022
There’s no proof that this fling ever went on, but one thing’s for sure – Drake treated her to a bunch of gifts from a Balenciaga store. In August 2022, CCTV footage of the pair emerged, showing them shopping together at the designer shop. Cecilia, who starred in Drizzy’s Wait For You video was apparently allowed to pick out anything she wanted from the store and spent a whopping $300k on her.
It’s clear that Drizzy is a fan of wining and dining a number of beautiful ladies, but maybe he still hasn’t found the one for him yet. We’re not complaining though – the more heartbreak he faces, the more songs and inspiring quotes he writes to help us through any post-breakup blues.
Which girl from this dating history do you think is best matched with Drake? Let us know in the comment section below!
This article was originally published in November 2018.
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