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The Ultimate Timeline Of Kylie Jenner's Boyfriends: From Tyga To Timothée Chalamet's Red Carpet Debut In 2025

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Kylie Jenner's love life has consistently been a source of intense global fascination, mirroring the dramatic highs and lows often seen on her family's reality show, *The Kardashians*. As one of the world's most successful beauty moguls, her romantic partners are instantly thrust into the spotlight, becoming major pop culture figures themselves.

As of December 21, 2025, the entrepreneur's dating narrative has entered a new, highly-buzzed-about chapter with an Oscar-nominated actor. This article provides the ultimate, updated timeline of the men who have held the attention of the Kylie Cosmetics founder, detailing the relationships that have shaped her life and image over the last decade.

The Men Who Captured the Mogul: A Complete Boyfriend Profile

Kylie Jenner's dating history includes a mix of rappers, actors, and fellow socialites. Each relationship, whether rumored or confirmed, has been a major media event, often influencing her personal brand and the narrative of the Kardashian-Jenner empire. Below are the most significant figures in her romantic history, including her current partner.

Timothée Chalamet (2023 – Present)

  • Full Name: Timothée Hal Chalamet
  • Date of Birth: December 27, 1995
  • Occupation: Actor (known for *Dune*, *Call Me By Your Name*, *Wonka*)
  • Relationship Timeline: First linked in April 2023, shortly after her final split from Travis Scott. The relationship was confirmed by sources throughout 2024 and they made a highly-anticipated red carpet debut at the 70th David Di Donatello Awards in Rome, Italy, in May 2025.
  • Key Details: This is arguably Kylie's most unexpected pairing, bridging the worlds of Hollywood prestige and reality TV royalty. The couple has remained relatively private, though their public appearances, including major award shows, continue to generate massive attention.

Travis Scott (2017 – 2022)

  • Full Name: Jacques Bermon Webster II
  • Date of Birth: April 30, 1991
  • Occupation: Rapper, Singer, Songwriter (known for *Astroworld*)
  • Relationship Timeline: On-again, off-again relationship from April 2017 to late 2022.
  • Key Details: The most defining relationship of her adult life, Scott is the father of her two children: daughter Stormi Webster (born February 2018) and son Aire Webster (born February 2022). They first connected at the Coachella Valley Music and Arts Festival in 2017 and maintained a complex, co-parenting relationship even during their breakups.

Tyga (2014 – 2017)

  • Full Name: Micheal Ray Stevenson
  • Date of Birth: November 19, 1989
  • Occupation: Rapper (known for "Rack City")
  • Relationship Timeline: Dated publicly from 2015 to 2017, though they were first linked in 2014.
  • Key Details: This was Kylie's first highly-publicized, long-term romance. Their relationship was a staple of the media cycle during the mid-2010s and was often featured on *Keeping Up with the Kardashians*. Despite their eventual split, Jenner has stated they will "always have a bond."

Jaden Smith (Rumored, Early 2013)

  • Full Name: Jaden Christopher Syre Smith
  • Date of Birth: July 8, 1998
  • Occupation: Actor, Rapper, Singer
  • Relationship Timeline: Widely rumored to be dating in early 2013.
  • Key Details: Often cited as Kylie's first serious, though never officially confirmed, romance. Jaden Smith is the son of Will Smith and Jada Pinkett Smith, and the two were part of the same young Hollywood social circle. Their connection is often referred to as her "first love."

The Evolution of Kylie Jenner's Dating Narrative

Kylie Jenner, who rose to fame on her family's reality show, has always had her personal life under a microscope. Her dating choices reflect her own evolution from a reality star to a global business powerhouse and a mother of two. The men she chooses are not just partners; they are essential entities in the narrative of her public life.

The Tyga Era: Teen Love in the Spotlight

The relationship between Kylie Jenner and Tyga dominated tabloid headlines for years. They first met at Kendall Jenner's 16th birthday party in 2011, but their romance didn't ignite until years later. The three-year relationship was marked by lavish gifts, red carpet appearances, and constant media scrutiny. The dynamic was a key storyline in the early days of Kylie's independent fame, setting the stage for the intense public interest that would follow her future relationships.

The end of their relationship in 2017 coincided with a major shift in Kylie's life, as she focused on expanding her Kylie Cosmetics brand and moving into a more mature phase of her career.

Travis Scott: Family, Fame, and Co-Parenting

The transition from Tyga to Travis Scott was swift and unexpected. The duo's connection at Coachella in 2017 quickly escalated into a serious relationship. Within months, the couple was expecting their first child, Stormi Webster, a pregnancy that Kylie famously kept entirely private until after the birth in February 2018.

Their on-again, off-again status became a defining element of their nearly five-year relationship. Despite the breakups—one in late 2019 and the final one in late 2022—they remained dedicated co-parents to both Stormi and their son, Aire Webster. The complexity of their bond—part romance, part family unit—demonstrated Kylie's commitment to prioritizing her children above all else.

The Timothée Chalamet Chapter: A New Level of Privacy and Prestige

Kylie Jenner's current relationship with Oscar-nominated actor Timothée Chalamet marks a significant departure from her past high-profile romances. The pairing, which began in 2023, has been notably more discreet and less integrated into her public-facing, reality-TV life.

The initial rumors of their romance sparked a frenzy across social media, with many fans calling it the most surprising celebrity coupling of the decade. Chalamet, known for his roles in prestige films like *Dune* and *Call Me By Your Name*, represents a shift towards a more traditional Hollywood partner, contrasting with her history of dating musicians.

Despite the couple's efforts to maintain privacy, their relationship has continued to flourish. Their joint appearance at the 2025 David Di Donatello Awards in Rome was a watershed moment, serving as their official red carpet debut and silencing persistent breakup rumors that had circulated earlier in the year. Sources close to the couple indicate that the relationship is "still going strong," with Chalamet reportedly very supportive of the billionaire beauty mogul's business ventures and her role as a mother.

This chapter signifies a more mature and guarded Kylie Jenner, who is balancing her massive business empire, motherhood, and a serious relationship away from the constant, unfiltered lens of reality television. The power of the Jenner-Chalamet pairing continues to be a top-tier celebrity story, proving that Kylie’s love life remains one of the most compelling narratives in modern pop culture.

Whether this romance with the *Dune* star will lead to another long-term commitment remains to be seen, but for now, Kylie Jenner is navigating a new, high-profile romance that keeps the world captivated.

kylie jenner boyfriends
kylie jenner boyfriends

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