In his feelings: A look back at Drake's romantic history

It was the one that everyone thought would last. The What’s My Name collaborators met in May 2009 and added fuel to their relationship with low-key date nights. The Diamond singer was also the inspiration behind some of the rapper’s biggest hits. Sadly, after a sweet encounter at the MTV VMAs and matching shark tattoos, the pair parted ways and ended what many hoped would be hip-hop’s next big power couple..

Before Rihanna came into Drake's life, the singer had a romantic relationship with Canadian singer Keshia Chante, who is rumored to be his childhood love.

In the song My Feelings, released in July 2018, the rapper mentions a woman named "Keke", who could be which could be short for Keshia. “Keke do you love me? Are you riding," he sings in the viral hit.

Jade grew up in Toronto with the rapper and was thought to be his "first great love." In his song Karaoke, Drake admits that he had plans of marrying his childhood sweetheart.

“Isn’t it ironic that the girl I wanna marry is a wedding planner? It tells me my life’s too much and it moves to Atlanta.”

Bria and Drake dated from 2008 to March 2009. In true Drake fashion, Bria couldn't escape their love without a couple of mentions in songs.

Young Money made them family, but their claims of marriage had many fans questioning their relationship status. The Moment for Life collaborators said that they were together on mulitple occasions.

These days, the rumors have been squashed as Nicki is engaged to her childhood love and she and track haven't been in contact since they both left the record label.

In 2014, Zoe and Drake sparked relationship rumors when they appeared on each other's social media. In 2018, the pair got close during a Golden Globes party. Now, Zoe is married to Karl Glusman.

Though they never attended any events together, Drake did go to many of Serena Williams' games. He was thought to be with her during 2015.

The rapper's admiration for the tennis player began in 2011, but it was not until 2015 that they were seen kissing in Cincinnati. The pair denied the relationship and Serena went on to marry Alexis Ohanian in 2018.

The 6 God and Jenny from the Block had everyone in their feelings when they appeared snuggled close in a series of social media photos. The pair claimed it was for a "special project," but fans had other speculations.

Drake rapped about their love in the songs Free Smoke, God's Plan and Diplomatic Immunity. JLo later responded to the rapper's claims by playfully calling him a "booty call."