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The Full Timeline: 8 Major Relationships That Define Kylie Jenner's Dating History (Updated 2025)

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Kylie Jenner's dating history is one of the most intensely scrutinized timelines in modern celebrity culture, an intricate web of high-profile romances that have played out across reality television, social media, and red carpets. As of December 2025, the global entrepreneur is navigating her latest, and perhaps most surprising, relationship with Oscar-nominated actor Timothée Chalamet, a pairing that continues to fascinate fans and media alike. This deep dive aims to separate fact from speculation, providing the most current and comprehensive look at the men who have shaped the life of the youngest member of the Kardashian-Jenner dynasty, from long-term co-parenting arrangements to her current, low-key romance.

The transition from reality TV star to global beauty mogul has been paralleled by an equally dramatic evolution in her personal life. The men in her life—from the rapper who fathered her two children to the indie actor she is currently linked to—have fundamentally influenced her public narrative. The ongoing nature of her current relationship, combined with the complexities of co-parenting with an ex, makes her romantic journey a compelling narrative that is constantly being updated.

Kylie Kristen Jenner: Biography and Profile

Kylie Jenner is not just a media personality; she is a powerful businesswoman and a cultural force whose life is documented for millions. Her personal history is inseparable from her professional empire.

  • Full Name: Kylie Kristen Jenner
  • Date of Birth: August 10, 1997
  • Age: 28 (as of December 2025)
  • Place of Birth: Los Angeles, California
  • Parents: Kris Jenner and Caitlyn Jenner (formerly Bruce Jenner)
  • Siblings: Kendall Jenner (full sister), and half-siblings Kourtney Kardashian, Kim Kardashian, Khloé Kardashian, and Rob Kardashian.
  • Primary Career: Media personality, socialite, businesswoman, and model.
  • Notable Businesses: Kylie Cosmetics (launched in 2015), Kylie Skin, and Kylie Swim.
  • Reality TV: Starred in Keeping Up with the Kardashians (2007–2021) and the Hulu series The Kardashians (2022–present).
  • Children: Stormi Webster and Aire Webster (with Travis Scott).
  • Net Worth: Estimated at around $700 million in 2024, derived primarily from her beauty and fashion ventures, despite being stripped of her "self-made billionaire" title by Forbes in 2020.

The Unexpected Romance: Kylie Jenner and Timothée Chalamet (2023–Present)

The relationship between Kylie Jenner and actor Timothée Chalamet is arguably her most surprising pairing to date, merging two drastically different worlds: the Hollywood indie scene and the global reality TV empire.

The Timeline of 'Kylothée'

Rumors of a romance between the two first began circulating in April 2023, shortly after Jenner's final split from Travis Scott.

  • April 2023: Initial reports surface linking the beauty mogul and the Dune actor, with sources suggesting they had been casually dating.
  • September 2023: They made their first high-profile public appearance together at a Beyoncé concert in Los Angeles, where they were seen kissing and interacting openly, confirming the speculation.
  • January 2024: The couple made a rare joint appearance at the Golden Globe Awards, where they were photographed together, solidifying their status as a major Hollywood power couple.
  • 2025 Status: The relationship remains relatively private, with the couple rarely making public appearances together, which often fuels speculation about their status. Despite their low-key nature, the relationship has continued into 2025, demonstrating a serious, committed partnership outside of the intense public scrutiny that defined her previous romances.

The pairing is notable for its discretion, a stark contrast to the highly publicized nature of her relationships with both Travis Scott and Tyga. Chalamet, known for his critically acclaimed film roles, and Jenner, the face of a massive cosmetic brand, represent a fascinating cultural crossover.

The Co-Parenting Era: Kylie Jenner and Travis Scott (2017–2023)

Kylie Jenner's relationship with rapper Travis Scott (born Jacques Bermon Webster II) was her longest and most significant, defining a five-year period of her life and resulting in two children.

A Tumultuous, On-Again, Off-Again Romance

Their relationship began swiftly after they met at the Coachella music festival in April 2017, where Scott was performing.

  • First Meeting (April 2017): The two connected at Coachella and quickly began dating.
  • First Child (February 2018): Jenner gave birth to their daughter, Stormi Webster, keeping the pregnancy largely private.
  • First Split (October 2019): The couple decided to take a break from their romance after two years of dating, though they remained dedicated co-parents.
  • Reconciliation (2020–2021): They reconciled during the COVID-19 pandemic lockdown, choosing to spend time together as a family.
  • Second Child (February 2022): Their son, Aire Webster, was born.
  • Final Split (Early 2023): The relationship ended again in early 2023, with sources confirming the permanent separation.

The dynamic between Jenner and Scott has always been marked by deep affection, family commitment, and professional independence. Despite the romantic separation, they continue to prioritize their roles as co-parents to Stormi and Aire, often spending holidays and family events together, showcasing a modern co-parenting arrangement.

The Controversial Romance: Kylie Jenner and Tyga (2014–2017)

Before Travis Scott, Kylie Jenner’s most public and scrutinized relationship was with rapper Tyga (born Michael Ray Nguyen-Stevenson).

The romance began to garner significant media attention in 2014, when Jenner was still a minor and Tyga was in his mid-twenties. The age difference and Jenner's age at the time of the relationship sparked widespread controversy and intense media coverage.

  • Initial Rumors (2014): The pair were frequently seen together, though they did not officially confirm their relationship until Jenner turned 18 in August 2015.
  • Relationship Confirmation (August 2015): Following her 18th birthday, the couple became much more open about their relationship, appearing together on red carpets and social media.
  • Breakup (April 2017): Their on-again, off-again relationship officially ended in April 2017. Interestingly, this split coincided almost immediately with Jenner’s first meeting with Travis Scott at Coachella.

This period cemented Jenner's status as a tabloid fixture and coincided with the explosive growth of her social media presence and the launch of Kylie Cosmetics, making it a pivotal time in her life and career.

Early Flings and Rumored Connections

Kylie Jenner's dating history includes several other short-lived romances and rumored connections that pre-date her most high-profile relationships. These early links often occurred during her teenage years and were frequently documented on social media and in the reality shows.

  • Jaden Smith (2013–2014): Jenner and actor/musician Jaden Smith, the son of Will Smith, were frequently linked in the early 2010s. Though they never officially confirmed a romantic relationship, they were often referred to as a young couple and remain close friends.
  • Cody Simpson (Rumored): Before his relationship with Gigi Hadid, Australian singer Cody Simpson was briefly rumored to have dated Kylie Jenner.
  • Other Brief Links: Other names that have appeared in the tabloids include Miles Richie (2014) and Lil Twist (2014), though these were generally short-term or unconfirmed connections.

From teenage flings to her current, mature partnership with Timothée Chalamet, Kylie Jenner’s romantic history is a dynamic reflection of her journey in the public eye. Her ability to transition from a highly publicized, co-parenting relationship with a rap superstar to a private, unexpected romance with an acclaimed actor demonstrates her evolving control over her own narrative. As of late 2025, she continues to balance the demands of her massive business empire, her role as a mother to Stormi and Aire Webster, and her life as one-half of one of Hollywood’s most talked-about couples.

kylie jenner dating history
kylie jenner dating history

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