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5 Untold Secrets Behind Hailey Baldwin And Drake's Mysterious 2016 Fling—And Drake’s Shocking New Song Reference

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As of December 2025, the world knows Hailey Baldwin as the model, entrepreneur, and wife of pop superstar Justin Bieber, but a persistent, nearly decade-old rumor continues to resurface: her brief, mysterious entanglement with rap titan Aubrey Drake Graham. This story, which began with a high-profile Memorial Day party, is not just a footnote in celebrity dating history; it's a fascinating look at two stars navigating fame, friendship, and intense media scrutiny before their lives took dramatically different paths. The intrigue surrounding this rumored fling has recently spiked again, thanks to a specific lyric on one of Drake’s latest albums, suggesting that the Toronto rapper still holds a memory of their short time together. We dive deep into the timeline, the denials, the evidence, and the current-day fallout of this unexpected celebrity connection.

Hailey Rhode Bieber and Aubrey Drake Graham: A Dual Celebrity Profile

To fully understand the dynamic between the two stars, it is essential to review their individual paths to global celebrity.

Hailey Rhode Bieber (née Baldwin)

  • Full Name: Hailey Rhode Bieber (née Baldwin)
  • Born: November 22, 1996 (Age 29 in late 2025)
  • Birthplace: Tucson, Arizona, U.S.
  • Family: Daughter of actor Stephen Baldwin, niece of Alec Baldwin.
  • Career Highlights: American model, socialite, creative director, and entrepreneur. Began modeling career in 2014. Founder of the popular skincare brand, Rhode.
  • Marital Status: Married to singer Justin Bieber (since 2018).
  • Key Entities: Stephen Baldwin, Justin Bieber, Rhode Skincare, IMG Models, Alec Baldwin.

Aubrey Drake Graham

  • Full Name: Aubrey Drake Graham
  • Born: October 24, 1986 (Age 39 in late 2025)
  • Birthplace: Toronto, Ontario, Canada.
  • Family: Son of Dennis Graham and Sandi Graham.
  • Career Highlights: Canadian rapper, singer, songwriter, actor, and businessman. Credited with popularizing R&B sensibilities in hip-hop. Holds numerous chart records. Co-founder of the OVO Sound label.
  • Marital Status: Single (As of late 2025).
  • Key Entities: OVO Sound, 'Hotline Bling', 'Certified Lover Boy', Toronto Raptors, Lil Wayne, Pusha T.

The 2016 Fling: What Really Happened Between the Model and the Rapper

The entire Hailey Baldwin and Drake dating rumor timeline is incredibly short, spanning just a few days in May 2016. At the time, Hailey was 19 and Drake was 29, and she was in an 'off-again' period with her future husband, Justin Bieber.

1. The Memorial Day Party Spark

The initial connection was made at Drake's star-studded Memorial Day party in Los Angeles. Sources at the time reported that the two were seen getting "cozy," sparking immediate speculation that a new A-list couple was forming.

2. The West Hollywood Dinner Date

Following the party, the pair were spotted on a dinner date at the celebrity hotspot Ysabel in West Hollywood. The sighting was enough to send the rumor mill into overdrive, as it suggested a follow-up to their initial party interaction. Reports indicated they were bonding and enjoying each other’s company.

3. The 'Borrowed' Necklace Evidence

Perhaps the most compelling piece of 'evidence' for a brief romance was a subtle fashion choice. Drake was later spotted leaving a different venue, The Nice Guy, wearing a small Gothic letter pendant necklace. This was the exact same piece of jewelry that Hailey Baldwin had been seen wearing twice before. This highly scrutinized detail led many to believe they were sharing accessories, a classic sign of a budding, albeit casual, relationship.

Hailey’s Public Denial and The 'Great Friend' Status

Despite the dinner date, the cozy party reports, and the shared jewelry, Hailey Baldwin quickly shut down the dating narrative. In a red carpet interview shortly after the rumors broke, the model was clear about her relationship with the Canadian superstar.

She stated that she and Drake were nothing more than "great friends." She further clarified, saying, "I've known [Drake] for a while, not like a long time, but we're just friends." This public statement effectively ended the media speculation at the time, confirming their interactions were platonic or, at most, a very brief, uncommitted fling.

The relationship was never formally confirmed by either party as a serious romance, cementing its status as one of the most intriguing and short-lived celebrity dating rumors of the mid-2010s. For Hailey, this brief period was a precursor to her eventual, and highly publicized, reunion and marriage to Justin Bieber.

The Shocking New Song Reference in 'Bahamas Promises'

The story of Hailey and Drake lay dormant for years until Drake released his album 'For All The Dogs' in late 2023. Track number 10, "Bahamas Promises," immediately grabbed headlines for an alleged, thinly veiled reference to Hailey Bieber.

A Lingering Memory in the Lyrics

The song is widely believed to address their brief 2016 encounter. In the track, Drake sings about a girl named 'Hailey' who he had a short, memorable experience with. The lyrics hint at a desire to rekindle a past, short-lived romance, suggesting that the model left a lasting impression on the prolific rapper.

The line is seen by many fans and entertainment analysts as Drake finally "speaking out" about the affair, albeit indirectly and years after the fact. The reference is a powerful example of how celebrity history, especially involving high-profile names, can be immortalized and reignited through music.

The Current Context and Topical Authority

The resurfacing of this rumor via Drake’s music highlights the complex web of relationships in the celebrity world. Hailey Bieber is now a married woman, a successful entrepreneur with her Rhode brand, and a key figure in the fashion and beauty industries. Drake, meanwhile, continues his reign as one of the most dominant forces in global music.

The fact that Drake chose to nod to the 2016 interaction in a recent album, despite Hailey’s marriage to his contemporary, Justin Bieber, underscores the enduring curiosity surrounding this almost-romance. It serves as a reminder that in the world of Hollywood, even the shortest flings can become pop culture legends.

hailey baldwin and drake
hailey baldwin and drake

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