Drake (born Aubrey Drake Graham) is turning 31 on Oct. 24, 1986 — meaning the handsome rapper has finally reached his prime. With a new year of life on the horizon, we wonder if Drake will finally find his Mrs. Right (or keep settling for Ms. Right Now)? Join Wonderwall.com as we take a look back at all the women Drake is rumored to have romanced over the years. Plus keep reading to find out which ladies inspired some of his most infamous songs…
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2005: Tika Sumpter
In 2005, before Drake became a world-famous rapper, he was a young Canadian actor on "DeGrassi: The Next Generation" who had a romantic moment with another up-and-coming star, actress Tika Sumpter. Not much is known about their date (or if there was more than one), but Tika shared in 2011 that they went out to dinner when she was working as a host on the Nickelodeon show "Best Friends Date" and has had a crush on him ever since.
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2005: Kat Dennings
In 2013, Drake appeared on "The Ellen DeGeneres Show" and shared with the host that years ago, he went on a date with actress Kat Dennings, saying he'd "always had a thing for her." Kat later clarified the matter with Chelsea Handler, saying it was more of a "non-date" that was totally overwhelming. Apparently Kat, who at the time was just 19, came home from their sushi dinner together to find numerous angry tweets directed at her for stealing Drake from his devoted fans. Now, she claimed, she'd be too terrified to date the rapper, saying, "I feel like I would die. Some Twitter person is, like, watching my tweets to see where I'm going."
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2009: Bria Myles
If you've listened to "Bria's Interlude" from Drake's 2009 album "So Far Gone," you can thank Bria Myles for the track. The rapper reportedly dated Bria for a short while, although he's never specifically confirmed (or denied) their relationship. In a 2017 interview, Bria was asked point-blank if she dated Drake, which she confirmed. When asked if he was good in bed, she giggled and refused to answer, which we all know means, "HECK, YES."
2009: Zineb Samir
Zineb Samir (seen here in 2016) was reportedly one of Drake's first major loves. Known as "Nebby," it's clear she gave Drake some major feels as he mentioned her in his song "Look What You've Done" with the lyrics: "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 rumored that his other hits "Best I Ever Had" and "Hotline Bling" are also about his relationship with her.
2009 and 2013: Teyana Taylor
In 2009, actress, model, dancer and singer Teyana Taylor posted a few pics of her and (then) up-and-coming rapper Drake getting cozy together. One pic in particular had Drake moving in for a kiss. Teyana claimed they were just "besties," but it was enough to get the rumor mill started about a possible love connection. Fast-forward to 2013 when Drake uploaded a pic of him cuddling with Teyana (with his face nestled in her hair) and, once again, rumors of a relationship were buzzing. Nothing more ever came of the rumors and we aren't sure if the two actually dated or were just BFFs as Teyana claimed.
2009 – ?: Rihanna
Ever since 2009, rumors have swirled about Drake and Rihanna having an on-again, off-again romance. It didn't help that in 2010, Drake gave an interview to The New York Times in which he claimed Rihanna used him like a "pawn" — which he later clarified was more about his own feelings of nervousness being around the beautiful singer. Over the years, claims there was a relationship between the two continued to heat up then die back down. In 2012, Drake and singer Chris Brown's entourages got into a club brawl — reportedly sparked by their mutual affection for Rihanna. Before the fight broke out, Drake reportedly returned a bottle of champagne Chris had sent to his table with a note saying, "I'm still f—ing Rihanna." In 2016 at the MTV Video Music Awards, Drake professed his love for Rihanna on stage, reigniting our hope they'll just get married and have babies already. Sadly, it seems as if their one-time love is on the back burner once more, but they've never stopped being the best of friends who routinely show up for one another's performances and make appearances on each other's songs.
2010: Maliah Michel
For a brief period in 2010, Drake reportedly dated an exotic dancer by the name of Maliah Michel. He was so smitten with her that he even asked her to appear in the music video for his hit song "Find Your Love" that same year. When Maliah was asked in 2011 why they broke up, she said she wasn't sure, but thinks it was his friends whispering in his ear about her career. She also said that Drake was always a "perfect gentleman" while they were together. However, in 2017 after Drake unceremoniously "retired her jersey" during Houston Appreciation Week, Maliah took to Instagram to let everyone know no man could do that, writing, "I'm shaking this azz into a wheel chair. Maliah will retire Maliah."
2011: Dollicia Bryan
Over the holidays in 2011, Drake hooked up with model (and serial rapper-dater) Dollicia Bryan. While the pair seemed happy, they reportedly broke up just a few months later after arguing over Drake's colored contacts while out to dinner at Villa Blanca in Los Angeles. To make it clear they were done, Drake allegedly invited ex-girlfriend Nebby to celebrate the 2012 New Year with him.
2013: Cyn Santana
A year before model and video vixen Cyn Santana was cast on the hit VH1 reality series "Love & Hip Hop," she briefly dated Drake in 2013 after they met on the set of 2 Chainz's video shoot for "No Lie." The pair were spotted together in numerous places for the next few months but the relationship was never confirmed by either side and seemed to fade away as quickly as it began.
2013: Tatyana Ali
In January 2013, word spread that former "Fresh Prince of Bel-Air" star Tatyana Ali and Drake had hooked up at her birthday party. The rumors heated up when Tatyana said in a Huffington Post interview that one-night stands were one of her guilty pleasures. However, Tatyana cleared up the confusion on "The Real" and said she and Drake didn't hook up. Maybe, but in Drake's 2013 song "Tuscan Leather," he said, "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." You be the judge.
2013: Tyra Banks
Ellen DeGeneres knows how to get Drake talkin' and that's exactly what he did in September 2013 when he admitted to the daytime talk show host that he went on a date with "America's Next Top Model" mogul Tyra Banks. Although he didn't share when the two dated, he admitted to taking Tyra, in disguise, to Disneyland. Tyra later spoke with Steve Harvey and cleared up the rumors in a freestyle rap where she confirmed there was a date to the theme park but that Drake wasn't her man, "yet."
2013 – 2014: Zoe Kravitz
The brief romantic relationship between Drake and actress Zoe Kravitz might have flown under the radar and vanished into obscurity if not for a 2017 episode of Andy Cohen's "Watch What Happens Live" on which Zoe appeared as a guest. When a caller asked Zoe if the rumors about her dating Drake were true, Zoe coyly responded with, "We hung out for a minute." It seems their relationship started in late 2013 and ended shortly after in 2014. While there wasn't much evidence of their romance, a few grainy pictures (including one of Zoe affectionately caressing Drake's face at a concert) also add credence to claims they were indeed an item.
2015: Serena Williams
Since 2011, there have been rumors about Drake and tennis legend Serena Williams engaging in a steamy, secretive romance. The two were often seen together smiling and Drake posted a suggestive tweet in '11 stating he couldn't wait to "put it on" her and make her sweat — during their match. Serena's ex-boyfriend, rapper and actor Common, also admitted in 2012 he was upset with Drake over Serena's "growing relationship" with him. It seems that even with all the evidence to the contrary, the two probably were just friends. However, in 2015, that changed when a photographer snapped a grainy picture of what appeared to be Drake and Serena making out at a restaurant. From there, Drake was seen at all of Serena's matches, even the semi-finals of the U.S. Open, which she lost. Fans immediately began blaming Drake for her bad luck. It seems that the pair parted ways a few months later with neither side ever confirming they'd dated.
2016: Jennifer Lopez
In December 2016, fresh off the heels of the latest media frenzy about Drake and Rihanna supposedly dating after he professed his love for her at the MTV Video Music Awards, the rapper threw a wrench into the rumor mill by sharing this Instagram picture of himself and Jennifer Lopez looking incredibly cozy with one another. J.Lo went on to post a pic of the two full-on cuddling and later, photos emerged of the pair spending New Year's Eve together. However, if there really was a serious romance — they two were also working on a song together at the time — it ended not long after it began. In March 2017, Jenny from the block claimed, "I am not with Drake." Just days later, she was seen on the arm of her current beau, baseball star Alex Rodriguez.
2017: Nicki Minaj
Since 2010, Drake has made no secret of his affections for fellow rapper and singer Nicki Minaj. On the track "Miss Me" from his debut album "Thank Me Later," Drake said, "I love Nicki Minaj / I told her I'd admit it / I hope one day we get married just to say we f—ing did it / and girl I'm f—ing serious I'm with it if you with it / 'cause your verses turn me on and your pants are mighty fitted." Although both Nicki and Drake have publicly stated they've never dated (Drake even rapped about not hooking up with Nicki on her 2014 song "Only" — although he also said he'd be "first in line" when she was single), fans have long wondered if and when the two might take their relationship to the next level. In January 2017, Nicki and rapper boyfriend Meek Mill called it quits, which coincided with the end of Drake's alleged relationship with Jennifer Lopez. In August 2017, the pair were seen sneaking out the back alley of a nightclub at 3 a.m., seemingly hoping to avoid paparazzi. But photogs were ready and waiting and snapped pictures of the two together, leading fans to hope it might finally be the real thing. If it was, it likely didn't last long because in September, Nicki was seen making out with rapper Nas at his 44th birthday party and had admitted all the way back in May the two had "sleepovers."