42 Diamonds And A Decade Of Drama: The Definitive Timeline Of Who Drake Has Dated (2025 Update)
The world of Aubrey "Drake" Graham's romantic life is as complex and heavily scrutinized as his lyrical catalog. As of December 18, 2025, the Canadian superstar continues to be the subject of intense speculation, with every dinner date, Instagram comment, and musical lyric sparking a fresh round of 'who is Drake dating now?' rumors. He has built a reputation not just as a music mogul but as the "Certified Lover Boy" whose relationships, whether fleeting or long-term, consistently dominate pop culture headlines and often inspire his biggest hits.
The rapper's dating history is a star-studded, decades-long timeline featuring pop icons, professional athletes, and rising models. This article cuts through the gossip to provide a definitive, updated look at the women who have captured the heart of the OVO founder, chronicling the most significant, and most recent, chapters in his storied love life.
Aubrey "Drake" Graham: A Biographical Profile and His Star-Studded Relationship History
The man behind the music, Aubrey Drake Graham, was born on October 24, 1986, in Toronto, Ontario, Canada. His journey to global stardom began not in a recording studio, but on the set of the Canadian teen drama Degrassi: The Next Generation, where he played Jimmy Brooks from 2001 to 2008.
- Full Name: Aubrey Drake Graham
- Born: October 24, 1986 (Toronto, Ontario, Canada)
- Occupation: Rapper, Singer, Songwriter, Actor, Record Producer
- Key Career Highlights: Credited with popularizing R&B sensibilities in hip-hop, co-founder of the OVO Sound label, multiple Grammy Awards, and breaking countless streaming records.
- Notorious Romantic Fact: In December 2022, Drake made headlines for commissioning a custom necklace, "Previous Engagements," featuring 42 diamonds—one for every time he considered proposing to a woman.
Drake’s dating timeline is a sprawling narrative, but it can be distilled into a list of his most notable and recent connections, categorized by their public status.
The Pantheon of High-Profile Romances (Confirmed and On-Again-Off-Again)
These are the women whose relationships with Drake defined eras of his career and resulted in some of his most memorable musical references.
Rihanna (2009 – 2016)
The most iconic and enduring relationship in Drake’s history is his on-again, off-again romance with pop superstar Rihanna. Their chemistry was undeniable, both on and off the stage, collaborating on hits like "Take Care," "What's My Name?," and "Work." Their relationship timeline was a decade-long saga of public flirtations, rumored splits, and emotional lyrical references. Drake famously declared his love for her at the 2016 MTV Video Music Awards, calling her "someone I’ve been in love with since I was 22 years old."
Jennifer Lopez (2016 – 2017)
The brief but highly publicized "Dra-Lo" romance began in late 2016. The pair shared cozy photos on social media, sparking a media frenzy. While the relationship was short-lived, it was a moment where two of the biggest names in music unexpectedly connected, creating a shockwave in the celebrity gossip world.
Serena Williams (Rumored 2011 & 2015)
Drake and tennis legend Serena Williams were frequently linked over several years. They were spotted together multiple times, including courtside at her matches. While neither star ever fully confirmed the relationship, the persistent rumors and public sightings solidified her place in the "Drake's love interests" narrative, often cited as one of his most significant, albeit private, connections.
SZA (Confirmed by Drake)
The relationship between Drake and R&B artist SZA was a surprise reveal. In his 2020 song "Mr. Right Now," Drake rapped the line, "Yeah, said I used to date SZA back in '08." SZA later clarified the relationship, stating it was "youth vibes" and "childish" and that the timeline was slightly off, confirming a connection but downplaying the intensity. This lyrical reference is a prime example of how Drake uses his music to confirm past private entanglements.
The Latest and Most Intense Rumors: 2023–2025
In the last few years, Drake has gravitated toward artists and influencers, often sparking rumors through cryptic social media posts or public outings. These recent connections are crucial for understanding his current dating landscape.
The 2024/2025 Connections: Brooklyn Nikole and Sexyy Red
Brooklyn Nikole (Rumored March 2024)
Model and Influencer. Brooklyn Nikole, a model and the sister of rapper Latto, became one of Drake's most recent rumored partners in early 2024. The speculation ignited when the two were spotted leaving a restaurant arm-in-arm in March 2024, followed by an entourage. Born July 19, 2002, in Atlanta, GA, Brooklyn Nikole is a prominent figure in the modeling and influencer world, representing a new generation of women Drake has been linked to.
Sexyy Red (Rumored 2023 – 2024)
American Rapper. Rumors of a romance between Drake and St. Louis rapper Sexyy Red (born Janae Nierah Wherry, April 15, 1998) circulated heavily throughout late 2023 and early 2024. The speculation was fueled by their close public interactions, including a photo Drake shared on social media calling her his "rightful wife." While the relationship status was never officially confirmed, their constant appearances together on tour and social media made them one of the most talked-about rumored couples of the year.
Lilah Pi (Rumored June 2023)
British Artist and Model. Drake seemingly confirmed a relationship with London-based artist Lilah Pi in June 2023. He sparked romance rumors by posting a touching birthday tribute to her, calling her his "inspo" and "my heart." Lilah Pi is known for her soulful, genre-fluid music and modeling work. This connection became a significant talking point among fans due to Drake's unusually public show of affection for a rumored partner.
More Notable Entanglements and Lyrical Inspirations
Beyond the major headlines, Drake’s history is peppered with numerous short-term flings and rumored connections that often find their way into his music, solidifying his status as the "Certified Lover Boy."
The List of Confirmed Dates and Persistent Rumors
Drake's romantic life is often a blend of reality and promotion, making it difficult to distinguish a serious relationship from a brief fling or a strategic photo opportunity. The following women have all been linked to the rapper, adding layers to his complex dating history:
- Johanna Leia: A model and mother of a basketball player, she was rumored to be dating Drake in 2021 after they were seen on a private date at Dodger Stadium.
- Julia Fox: The actress and model confirmed that she went on a date with Drake in February 2022, calling him a "great guy and a gentleman." The date reportedly took place before her high-profile relationship with Kanye West.
- Kylie Jenner: Rumors of a casual relationship between the reality star and the rapper surfaced in late 2019 and early 2020.
- Zmeena Orr: Model and influencer who has been alleged to be one of Drake's girlfriends.
- Chantel Everett & Riley Simpson: Both women were rumored to have hooked up with Drake in 2022, according to various celebrity gossip sites.
- Bria Vinaite: The actress was linked to Drake in 2017.
- Imaan Hamman: The model sparked romance rumors with Drake in February 2020 when they were seen walking arm-in-arm during New York Fashion Week.
- Lexi Wood: A model who was rumored to be his most recent public pairing in May 2025, though neither confirmed or denied the relationship.
The "42 Diamonds" and the Lover Boy Legacy
The sheer number of women linked to Drake—from pop culture royalty to rising social media stars—speaks to his unique position in the celebrity landscape. His 42-diamond necklace, which represents the number of times he wanted to propose, is a physical manifestation of his romantic intensity and his inability to settle down. It highlights a central theme in his music and life: the pursuit of love, the difficulty of commitment, and the lingering presence of past relationships.
Whether he is dropping a new album or simply stepping out for dinner, the question of "who is Drake dating" remains one of the most persistent and engaging topics in entertainment news. As the end of 2025 approaches, the world waits to see which name will be the next to join the ever-growing, legendary list of women who have inspired the Certified Lover Boy.
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