25+ Women Who Have Dated Drake: The Definitive Timeline Of His Exes And 2024 Romances
Drake’s love life has always been as headline-grabbing as his music career, a complex web of high-profile relationships, brief flings, and lyrical confessions that span over a decade. As of December 20, 2025, the rapper continues to fuel speculation with new rumored connections, keeping fans and the media constantly guessing about the woman currently holding his attention.
From his iconic, on-again-off-again romance with Rihanna to the most recent 2024 sightings with Brooklyn Nikole, the younger sister of rapper Latto, Drake’s dating history is a masterclass in celebrity intrigue. This article provides the definitive, updated timeline of the women who have inspired his biggest hits and the latest details on his most recent high-profile connections.
The Definitive Timeline: A List of Drake's Exes and High-Profile Romances
Drake, born Aubrey Graham, has been linked to dozens of women throughout his career. While many relationships remain unconfirmed rumors, a significant number of high-profile connections have been acknowledged by either Drake, the woman involved, or through undeniable public evidence. This list details some of the most famous and influential women in his dating history, serving as a comprehensive biography of his romantic life.
- Rihanna (Musician/Entrepreneur): The most iconic and turbulent of Drake's relationships. Their on-again, off-again romance spanned nearly a decade, from 2009 to 2016. Drake publicly declared his love for her at the 2016 MTV VMAs.
- Serena Williams (Tennis Legend): Drake and the tennis star were rumored to be dating on and off between 2011 and 2015. Drake was frequently seen at her matches, and in a fresh 2024 update, he revealed his song "Too Good" is about her.
- Jennifer Lopez "J.Lo" (Musician/Actress): Their brief but highly publicized romance took place in late 2016 and early 2017. The relationship was confirmed by cozy Instagram photos and a joint New Year's Eve appearance.
- Kylie Jenner (Media Personality/Entrepreneur): Rumors of a romance sparked in late 2019 after the two were reportedly "attached at the hip" at Drake's 33rd birthday party, shortly after her split from Travis Scott.
- SZA (Musician): The R&B star confirmed in 2020 that she briefly dated Drake around the end of 2009. She clarified the timeline to ensure no "underage or creepy" implications were made, as she was 19 at the time.
- Julia Fox (Actress/Model): In 2022, Fox revealed she had a brief, high-profile "hanging out" period with Drake around 2020, prior to her relationship with Kanye West. She confirmed he bought her two Birkin bags and flew her to his Toronto mansion.
- Johanna Leia (Model/Mother): Drake dated the mother of young basketball phenom Amari Bailey for several months in 2021. Their romance made headlines when they were spotted on a private dinner date at an empty Dodger Stadium.
- Bria Myles (Model/Actress): A past flame whose name is often cited as the inspiration for the lyric "Bria's Interlude" on his 2009 mixtape So Far Gone.
- Catya Washington (Reality Star): Linked to Drake in the early days of his career around 2010.
- Ericka Lee (Model): An early love interest who was involved in a legal dispute with Drake over songwriting credits for "Marvin's Room."
- Keisha Chanté (Musician/Actress): Drake's first love and childhood friend from Toronto, whom he has frequently mentioned in his music and interviews.
- Tyra Banks (Supermodel/TV Personality): The two were rumored to have briefly dated around 2013, with Drake later featuring her in his "Child's Play" music video, referencing a date they had at The Cheesecake Factory.
- Malaika Terry (Model): Linked to the rapper in 2018.
- Zoe Kravitz (Actress): They were rumored to have dated briefly in 2014.
- Hailey Bieber (Model): Rumored to have been a brief fling around 2016.
The Latest Headlines: Who is Drake Linked to in 2024?
Drake’s dating life in 2024 has been dominated by two high-profile, though very different, rumored connections. These recent developments show the rapper’s continued pattern of dating women who are either rising stars or within his immediate music circle.
The Brooklyn Nikole Rumors (March 2024)
The most recent significant speculation in 2024 centered on Brooklyn Nikole, the younger sister of Atlanta rapper Latto.
Rumors first ignited in March 2024 after a video surfaced showing Drake and Brooklyn, who is reportedly 21, leaving a dinner outing together. The alleged outing caused a stir online, primarily due to the 16-year age difference between the two. Neither Drake nor Brooklyn Nikole have officially confirmed a romantic relationship, but the public sighting was enough to fuel the rumor mill for months.
The Sexyy Red Connection (2023–2024)
Another prominent figure linked to Drake from late 2023 into 2024 is rising rapper Sexyy Red.
Their connection is often characterized as a blend of professional support and playful flirtation. Drake has publicly referred to Sexyy Red as his “rightful wife,” while she has called him her “man” on social media. While they have shared cozy photos and appeared together on tour, the general consensus is that their relationship is a close, highly visible friendship and professional mentorship, rather than a confirmed romance.
The Music Legacy: Which Songs Are About His Exes?
Drake is famous for wearing his heart on his sleeve—or, more accurately, in his lyrics. His discography is a rich tapestry of references, dedications, and subtle jabs aimed at his former flames, a practice he once admitted he regrets because of the "disrupting" effect on their lives.
Rihanna: The Muse and the Heartbreak
Rihanna is widely considered the primary muse for many of Drake's most emotional tracks. Songs like "Take Care," which features Rihanna herself, and "Fireworks" are thought to detail the early stages of their complicated dynamic. His lyrics often reflect a desire to save her or be the one to finally make her settle down, a theme that defined their long-standing relationship.
Serena Williams: The Private Power Couple
In a major 2024 revelation, Drake confirmed that his 2016 hit "Too Good" is about Serena Williams. Beyond that, the 2013 track "Worst Behaviour" contains a direct reference: "I'm with my whole set, tennis matches at the crib." These references highlight the private, on-and-off nature of their relationship before her marriage to Alexis Ohanian.
Jennifer Lopez: The Brief Winter Fling
The short-lived romance with J.Lo was quickly immortalized in his music. On the 2017 track "Free Smoke," Drake raps about drunk-texting Jennifer Lopez. Later, on "Diplomatic Immunity," he referenced the timing of their split, rapping: "2017 I lost a J. Lo." He also sampled her song "If You Had My Love" on his track "Teenage Fever."
The 'In My Feelings' Mystery
Perhaps his most famous reference is the 2018 hit "In My Feelings," which popularized the lines, "Kiki, do you love me?" The "Kiki" referenced in the song is widely believed to be Keshia Chanté, his childhood friend and first love, though the song's popularity led to a global dance challenge and immense speculation about the identity of the women mentioned.
Ultimately, Drake's songs serve as an unofficial, chronological diary of his romantic encounters. His willingness to integrate his personal life into his art ensures that his exes remain a crucial part of his public narrative and a key element of his topical authority in the music world.
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