Ah, Drake: Everyone’s favorite emotional rapper.
It has never been a cooler time to be an emotional music listener. Did you ever think that you would ever shed a tear while listening to rap when you were younger? I certainly didn’t.
In short, whatever Drake is feeling, you’re certainly feeling. Feeling elated in the morning? Drake has a song for that. Inconsolably miserable by the early afternoon? Drake has you covered, too. Need to get pumped up in the evening? Need I say more?
Regardless, the man is a talented musician, but like with all celebrities, most people are hopelessly fascinated with his love life and who he is currently dating. Drake is the ever-elusive rap good boy – and many women would fall over themselves to be with them. Only a select few have ever been so lucky to call them man theirs.
No, you’re not on the list (and I’m sorry).
Keshia Chante 2000-2002
Drake and Keshia Chante knew each other since they were younger. Drake even wrote a song about Keshia and said that he was “proud to say she is an ex.”
Chante stated that while their relationship was passionate, it was very difficult.
Jade Lee 2006-2006
Drake and Jade Lee dated back in 2006. He even raps about her in his songs, “Karaoke” and “Look What You’ve Done.”
However, it seems that the two are on good terms because Lee later Instagrammed a photo of the two with the caption, “10 years ago we [used] to dream about being a rapper and an event planner.”
Zineb Samir 2009Instagram.
Drake and Samir, also known as Nebby, dated for a short while back in 2009. Drake later revealed that he wrote “Look What You’ve Done,” a song off of his album, Take Care, about her. He also said during an interview with Toronto’s LOW 93.5 that “Best I Ever Had” was about her as well.
Cat Washington 2009Instagram.
Cat Washington said that she first met Drake on the set of “Best I Ever Had.” She said that the two were together for over a year. When asked about the relationship, she said, “It was a regular relationship. I was in love, but at the end of the day, he started getting a bit too loose.”
Drake and Rihanna first hooked-up at Lucky Strike bowling alley in New York.
Drake and Rihanna dated for a brief stint back in the summer of 2009. Rihanna was the one who called it quits.
After the relationship ended, Drake said, “I was a pawn,” and then added that Rihanna gave him a taste of his own medicine by romancing and then dumping him. Drake did not confirm that they were dating back in 2009 until several years later.
Maliah Michel 2010Instagram.
After appearing in Drake’s “Find Your Love” music video, Maliah and Drake began dating. The relationship was quiet until after the two broke up.
Michel, after the breakup, said, “Drake and I had a really great relationship sharing a really close bond. I don’t know if people really realized that…With Drake, he was always a gentleman. He was really sweet and he cared for me. He was great.”
Dollicia Bryan 2011
Drake and Dollicia Bryan met in January 2011 at Dollicia’s birthday party. Towards the end of 2011, Dollicia’s representative confirmed that the two were dating, but the relationship ended just a month later.
Serena Williams 2011
Serena Williams and Drake were first spotted together at the All England Club after Williams beat Victoria Azarenka. They had a brief relationship, which ended due to the rapper’s roaming eye once again.
Sophia Marie 2012
Drake was briefly linked to the model and dancer, Sophia Marie, in 2012 after she appeared in his music video for “Best I Ever Had.” There’s a reoccurring theme here.
Hailey Baldwin 2016
It seems that Drake took a four-year break to be single and find himself. He was briefly linked to Hailey Baldwin, but nothing was confirmed and the fling didn’t seem serious.
Their infamous romance was rekindled when they were spotted together, got matching tattoos and he confessed his love for her at the VMAs after her award-winning performance. Sadly, the relationship ended after some highs and lows between the pair.
Jennifer Lopez 2016
Rumors of a relationship began when the rapper was spotted at J.Lo’s Vegas show. It was said she even canceled a $1 million NYE performance to hang out with Drake and confirmed when the two posed for an intimate Instagram shot. In Drake’s song “Free Smoke” he raps that he drunk texts J.Lo.
Bella Hadid 2017
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@victoriassecret I am so excited!..!!!!Thank you @monica.mitro @10magazine @johndavidpfeiffer and of course the wonderful, incredible @ed_razek + everyone on the team for making this dream come true again.. I feel so crazy humbled to get the opportunity to be a part of this show again…Walking into the offices this year i felt so happy, healthy, and honored.. I can't wait for another incredible experience!!! Congrats to all of the beautiful ladies I will be walking beside. I can't wait! Xx 💕🌸
A love story heard many times, the model and the rapper. Bella and Drake were spotted at dinner and sources say that they are keeping it lowkey. But the couple may be going public sooner because allegedly Drake threw Bella a lavish 21st birthday party. Let’s just hope that if the two every breakup Bella and The Weeknd’s iconic Victoria’s Secret encounter isn’t recreated.Giphy
Can’t wait to see the two slay the red carpet together.
Malaika Terry 2018
Model Malaika Terry and Drake were spotted hanging out in May 2018. It was just him, Terry and his two security guards out with them making fans speculate that they were on a date. The two were seen in Toronto possibly holding hands.
Bella B Harris 2018
Rumors are circulating that Drake and model Bella B Harris are dating. Harris posted a photo of the two hanging out backstage during one of his New York City shows and they looked extra cute and comfortable around one another. Nothing is confirmed, but fans are speculating that the two are dating.
Drake is currently single, after getting out of a brief relationship with the 18-year old model, Bella Harris.