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The Weeknd's Heartbreak History: 7 High-Profile Relationships That Inspired His Darkest Hits

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The Weeknd's love life has always been as captivating, and often as melancholic, as the music he creates. For over a decade, the Canadian superstar, born Abel Tesfaye, has channeled his most intense romantic experiences—the whirlwind romances, the devastating breakups, and the private moments—into chart-topping albums that define the modern R&B sound. As of late December 2024, while reports suggest the artist is currently single, his most recent high-profile link remains a subject of intense curiosity, proving that the man behind the music is just as compelling as his cinematic, dark pop alter-ego.

This deep dive explores the complete relationship history of Abel Tesfaye, chronicling the influential women who have shaped his artistry and inspired the lyrical venom and vulnerability found on albums like After Hours and the deeply personal EP My Dear Melancholy,. From supermodels and pop princesses to his latest low-key partner, here is the definitive list of The Weeknd's most significant relationships.

Abel Makkonen Tesfaye: Complete Biography Profile

  • Full Name: Abel Makkonen Tesfaye
  • Stage Name: The Weeknd
  • Date of Birth: February 16, 1990
  • Age: 34 (as of late 2024)
  • Birthplace: Toronto, Ontario, Canada
  • Nationality: Canadian
  • Parents: Makkonen and Samra Tesfaye (immigrants from Ethiopia)
  • Occupation: Singer-songwriter, Record Producer, Actor, Businessman
  • Musical Genres: R&B, Pop, Trap, New Wave
  • Debut Album: Kiss Land (2013)
  • Breakthrough Albums: Beauty Behind the Madness (2015), Starboy (2016), After Hours (2020), Dawn FM (2022)
  • Notable Awards: 4 Grammy Awards, 20 Billboard Music Awards, 6 American Music Awards, 2 MTV Video Music Awards.
  • Acting Roles: Co-creator, co-writer, and star of the HBO series The Idol (2023).

The Definitive Timeline of The Weeknd's Most Influential Romances

The Weeknd's dating history is a complex web of on-again, off-again cycles, high-profile red carpet appearances, and private moments that were later exposed through his raw, confessional music. His knack for turning personal pain into pop gold is what gives his body of work its unique topical authority.

1. Bella Hadid (2015–2019: The On-Again, Off-Again Epic)

The relationship between The Weeknd and supermodel Bella Hadid is arguably the most defining romance of his career, spanning multiple years and inspiring some of his most profound artistic statements.

Their initial spark ignited in 2015 after they met at Coachella and later collaborated on an album project. Their first public appearance as a couple was at the 2016 Grammy Awards. This first chapter concluded in November 2016 due to their conflicting schedules.

The drama intensified when The Weeknd began dating Selena Gomez shortly after. Following his breakup with Gomez, he and Hadid were spotted together again in 2018, confirming their reconciliation. This second, more private phase lasted until August 2019, when they officially split again, citing distance and busy careers as the primary factors.

The Musical Impact: The 'After Hours' Entity

Many fans and critics believe that the entire After Hours album (2020), which birthed the massive hit "Blinding Lights," is heavily influenced by his final breakup with Bella Hadid. Songs like "Save Your Tears," "Heartless," and "Faith" are frequently analyzed as direct lyrical references to their turbulent, on-and-off relationship, painting a picture of regret, late-night partying, and the emotional toll of a celebrity romance.

2. Selena Gomez (2017: The Whirlwind Pop Crossover)

In a surprising twist that dominated celebrity headlines, The Weeknd began a relationship with pop star Selena Gomez in January 2017, just two months after his first split from Bella Hadid. This was a highly public romance, featuring red carpet debuts at the Met Gala and numerous international trips, instantly becoming a major pop culture moment.

Their relationship lasted about 10 months, ending in October 2017. The breakup was widely reported as amicable, attributed to the difficulty of maintaining a long-distance romance while both were on tour and filming projects.

The Musical Impact: The 'My Dear Melancholy,' Entity

The most direct musical evidence of this relationship came in 2018 with the release of the EP My Dear Melancholy,. The track "Call Out My Name" is universally accepted as a song about Gomez. The most shocking lyric is the line, "I almost cut a piece of myself for your life," which many believe refers to the rumor that The Weeknd considered donating a kidney to Gomez during her health struggles—a rumor that added a layer of profound, sacrificial love to the narrative.

3. Simi Khadra (2022–Present: The Private, Low-Key Link)

After a period of relative quiet in his dating life, The Weeknd was linked to DJ and fashion influencer Simi Khadra, one half of the twin DJ duo Simi and Haze. This relationship is notable for its extreme privacy, contrasting sharply with his previous high-profile romances.

Rumors began swirling in early 2022, and the couple was seen sharing a kiss at a Las Vegas club in February 2022. The relationship is particularly intriguing because Simi Khadra was reportedly once a friend of Bella Hadid, adding another layer of complexity to The Weeknd's social circle. While their public appearances are rare, they have been spotted together as recently as November, and some reports even mention an appearance at the 2025 Grammys, suggesting a quiet but ongoing commitment. This low-key approach with Simi Khadra suggests a shift towards valuing privacy over public spectacle in his personal life.

Other Noteworthy Entities and Rumors

Beyond the three main relationships, Abel Tesfaye has been linked to a few other high-profile figures, fueling the gossip columns and adding to his mystique as a modern R&B lothario.

Angelina Jolie (2021: The Power Dinner Entity)

In 2021, The Weeknd was repeatedly seen having dinner with Oscar-winning actress Angelina Jolie. While the nature of their connection was never officially confirmed—some speculated it was purely business related to his HBO project The Idol—the repeated outings at high-end restaurants in Los Angeles sparked intense rumors of a potential romance between the two global icons.

Rosalía (2020: The Collaboration Rumor)

Following their collaboration on the remix of "Blinding Lights," The Weeknd and Spanish singer Rosalía were spotted together, leading to brief speculation. However, this was largely considered a professional connection, with no confirmed romantic involvement.

Yovanna Ventura (2017: The Brief Fling)

Shortly after his breakup with Selena Gomez, The Weeknd was briefly linked to model Yovanna Ventura. They were seen holding hands at a party, but the connection appeared to be a short-lived fling, never escalating into a serious public relationship.

The Weeknd and The Art of Heartbreak: Topical Authority

The enduring fascination with The Weeknd's relationship history is not just about celebrity gossip; it's central to his brand as an artist. His ability to transform genuine emotional turmoil into critically acclaimed, commercially successful music is a masterclass in topical authority.

The narrative of the tortured artist, the "Starboy" who struggles to maintain a normal relationship amidst fame and hedonism, is woven into his DNA. The contrast between the emotional depth of tracks like "Wicked Games" and the high-octane pop of "Take My Breath" is a reflection of the internal conflict he often details in his lyrics—a conflict often born from his complicated romantic life.

Every major album release, especially After Hours and My Dear Melancholy,, is treated by fans as an emotional autopsy of his latest breakup. This cyclical process—date a celebrity, break up, release a hit album about the breakup—has solidified his status as one of music's most compelling and influential figures. It is a relationship with his audience built on shared vulnerability, making his love life an essential component of his artistic legacy.

the weeknd relationship
the weeknd relationship

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