20+ Women Drake Has Dated: The Complete Timeline Of The 'Certified Lover Boy's' High-Profile Romances (2009-2025)

Aubrey Drake Graham: The Profile of a Certified Lover Boy

The question of "who has Drake dated" remains one of the most enduring mysteries in pop culture, and as of late December 2025, the celebrated rapper continues to keep fans guessing about his official relationship status. The Canadian megastar, known for his emotionally charged lyrics and ability to turn a private moment into a global headline, has a dating history that reads like a celebrity A-list, spanning from music legends to reality stars and high-profile models. This comprehensive article delves into the full, up-to-date timeline of the women who have captured the attention of the man behind the music.

Aubrey Drake Graham, better known simply as Drake, has cultivated a reputation as a serial romantic, often immortalizing his former flames in his chart-topping songs. While he is currently believed to be single, his last rumored fling was a high-profile outing in March 2024, proving that the Certified Lover Boy's romantic pursuits are an ever-evolving story. To understand his complex love life, we must first look at the man himself.

• Full Name: Aubrey Drake Graham
• Date of Birth: October 24, 1986
• Birthplace: Toronto, Ontario, Canada
• Occupation: Rapper, Singer, Songwriter, Actor, Entrepreneur
• Known For: Popularizing R&B sensibilities in hip-hop, starring in *Degrassi: The Next Generation*, and hits like "Hotline Bling," "God's Plan," and "One Dance."
• Estimated Net Worth: Between $250 million and $400 million, positioning him as one of the wealthiest musicians globally.
• Child: Adonis Graham (with Sophie Brussaux)

The Definitive List of Drake's High-Profile Relationships and Rumors

Drake's love life is characterized by a mix of long-term, on-again-off-again romances and brief, highly-publicized flings. His tendency to reference past relationships in his music, such as the track "Mr. Right Now," often serves as a retroactive confirmation of a romance years later. This list compiles the most significant women linked to the hip-hop icon.

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The Iconic, On-Again-Off-Again Romances

The core of Drake's dating history involves two major, long-running relationships that defined different eras of his career:

1. Rihanna (2009–2016, On-Again-Off-Again)

Meeting in 2005, the relationship between Drake and Rihanna was perhaps his most high-profile and emotionally significant. Their on-again-off-again romance spanned nearly a decade, fueled by intense public speculation and lyrical exchanges. Drake's famous declaration of love for her at the 2016 MTV Video Music Awards remains a legendary pop culture moment. Their inability to settle into a permanent relationship has been a recurring theme in his music and public narrative.

2. Serena Williams (2011–2015, Rumored)

While never officially confirmed, Drake and tennis superstar Serena Williams were frequently photographed together, sparking intense dating rumors. He was often seen supporting her at major tournaments, and the pair were spotted kissing in 2015. The relationship was a significant source of media attention during its peak.

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The A-List Celebrity Flings

As his fame grew, Drake was linked to an array of fellow A-list stars, often resulting in brief but memorable flings:

• Jennifer Lopez (J.Lo) (2016–2017): Their short-lived romance was a major headline, marked by cozy social media photos and a rumored song collaboration. The relationship was notable for its unexpected pairing of two music titans.
• Kylie Jenner (2019–2020, Rumored): Following her split from Travis Scott, Drake and Kylie Jenner were rumored to be casually dating. They were seen together at various events, though the relationship was never formalized.
• SZA (2009, Confirmed Later): Drake's 2020 song "Mr. Right Now" revealed he had dated SZA back in 2008. SZA later clarified the timeline, stating the romance occurred in 2009 when they were both younger, adding a layer of retrospective intrigue to his history.
• Kat Dennings (2011, Brief Fling): The actress revealed in an interview that she and Drake went out for sushi just one time, confirming a brief, low-key encounter.
• Julia Fox (2020, Brief Fling): Before her high-profile relationship with Kanye West, Julia Fox had a brief romantic connection with Drake.

The Mother of His Son: Sophie Brussaux and Adonis Graham

One of the most defining relationships in Drake's life is with French artist Sophie Brussaux, the mother of his son, Adonis Graham. This relationship was initially shrouded in secrecy and controversy, only confirmed publicly after the birth of Adonis in October 2017.

The Relationship with Sophie Brussaux

Their connection began as a fling, but it resulted in the birth of his first child, a fact that was dramatically revealed to the world by Pusha T in the infamous 2018 diss track "The Story of Adidon." Drake later confirmed his fatherhood on his album *Scorpion*. Today, Drake and Brussaux maintain a strong, co-parenting relationship, often celebrating their son's birthday together, including a lively cowboy-themed party in October 2025.

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Brussaux, born in Bordeaux, France, is a talented celebrity portrait artist who previously worked in the adult film industry under the name Rosee Divine. She has since dedicated her life to art and co-parenting.

The Most Recent and Rumored Flings (2023–2025)

Even as one of the most successful artists in the world, Drake's dating life continues to generate buzz, with several rumored connections making headlines in the last two years.

Brooklyn (Latto's Sister) (March 2024): Drake was spotted having a public outing with Brooklyn, the younger sister of Atlanta rapper Latto, in March 2024. While neither confirmed a relationship, the sighting was his most recent public pairing at the time, sparking widespread speculation about a new romance.

Sexyy Red (2023–2024, Rumored): The "SkeeYee" rapper Sexyy Red was rumored to have hooked up with Drake in a casual fling that spanned late 2023 into 2024. The rumors were fueled by their public appearances and social media interactions.

Chantel Everett (2022, Rumored): The *90 Day Fiancé* star was rumored to have been linked to Drake in 2022, adding a reality TV personality to his diverse list of romantic interests.

Imaan Hammam (2020, Rumored): The Dutch-Egyptian-Moroccan supermodel was rumored to be Drake's last fling before he entered a period of relative quiet in his love life, with the pair spotted spending time together in early 2020.

Drake's Complete Dating History: A Timeline of Connections

Drake's romantic entanglements are complex, with many brief flings and collaborations blurring the lines between friendship and romance. Below is a more comprehensive list of the women he has been linked to over his career, showcasing the sheer breadth of his love life:

• Keshia Chante (Childhood Love/2000s)
• SZA (2009)
• Rihanna (On-Again-Off-Again, 2009–2016)
• Kat Dennings (2011)
• Serena Williams (Rumored, 2011–2015)
• Rita Ora (2012, Rumored)
• Zoe Kravitz (2013, Rumored)
• Sophie Brussaux (Mother of his son, Adonis, 2017)
• Jennifer Lopez (J.Lo) (2016–2017)
• Bria Vinaite (2017)
• Bella Harris (2018, Rumored)
• Kylie Jenner (Rumored, 2019–2020)
• Imaan Hammam (2020, Rumored)
• Julia Fox (2020)
• Chantel Everett (2022, Rumored)
• Riley Simpson (2022, Rumored)
• Sexyy Red (Rumored, 2023–2024)
• Brooklyn (Latto's Sister) (March 2024)

The "Certified Lover Boy" persona is a self-fulfilling prophecy for Drake, whose dating life remains a constant source of fascination. Whether he is dating a fellow superstar or a lesser-known personality, his romantic entanglements are always in the spotlight, forever intertwined with his musical career and his public image.