The Billion-Dollar Timeline: Unpacking Kylie Jenner's Most Talked-About Relationships (Updated 2025)

Contents
Kylie Jenner's romantic life has always been a primary point of fascination, evolving from teenage flings under the reality TV spotlight to high-profile, private relationships as an adult billionaire businesswoman. As of late 2025, the youngest Jenner is in a firmly established, yet famously low-key, relationship with Oscar-nominated actor Timothée Chalamet, a pairing that continues to surprise and captivate fans globally. This deep dive examines the full spectrum of her dating history, from her first loves to her co-parenting dynamic with Travis Scott, and the current status of her romance with the *Dune* star, providing the most up-to-date information on her relationships as of December 2025.

Kylie Kristen Jenner: A Complete Profile

Kylie Jenner, born on August 10, 1997, in Los Angeles, California, is one of the most influential media personalities and entrepreneurs of her generation. Her rise to fame began with the reality television series *Keeping Up With The Kardashians* (KUWTK) and continued with the launch of her highly successful beauty brand, Kylie Cosmetics. She is the youngest daughter of Caitlyn Jenner (formerly Bruce Jenner) and Kris Jenner.
  • Full Name: Kylie Kristen Jenner
  • Born: August 10, 1997 (Age 28 in 2025)
  • Birthplace: Los Angeles, California, U.S.
  • Parents: Caitlyn Jenner and Kris Jenner
  • Siblings: Kendall Jenner (full sister); half-siblings Kourtney Kardashian, Kim Kardashian, Khloé Kardashian, Rob Kardashian, Burt Jenner, Brandon Jenner, Brody Jenner, and Casey Jenner.
  • Occupation: Media Personality, Socialite, Businesswoman, Entrepreneur.
  • Known For: *Keeping Up With The Kardashians*, *The Kardashians*, Kylie Cosmetics, and The Kylie Shop.
  • Net Worth (2025 Estimate): Between $670 million and $750 million.
  • Children: Stormi Webster and Aire Webster (with Travis Scott).

The Early Years: From Jaden Smith to Tyga's Reign

Kylie Jenner's dating life first became public knowledge during her formative years on E!'s *Keeping Up With The Kardashians*. These early relationships often involved other young celebrities and laid the groundwork for the intense media scrutiny she would face later.

The First High-Profile Romance: Tyga (2014–2017)

The relationship between Kylie Jenner and rapper Tyga (Michael Ray Nguyen-Stevenson) was her first to draw significant, and sometimes controversial, media attention.

Their romance began to gain traction in 2014, though they did not confirm the relationship until Kylie turned 18 in August 2015.

The three-year, on-again, off-again relationship was heavily documented across social media and on the family's reality show, establishing Kylie as a major celebrity figure outside of her family's fame. Their relationship was characterized by lavish gifts, red carpet appearances, and a significant age difference that fueled tabloid headlines. They officially split in 2017.

Other Notable Early Flings

Before and during the Tyga era, Kylie was linked to several other names, though most were brief or unconfirmed.
  • Jaden Smith: The son of Will Smith was widely considered Kylie's first serious public relationship, with the pair linked as early as 2013. They maintained a close friendship after their romantic involvement ended.
  • Cody Simpson: The Australian singer was briefly linked to Kylie in 2011.
  • PartyNextDoor: Following a temporary split from Tyga in 2016, Kylie was rumored to be dating rapper PartyNextDoor (Jahron Anthony Brathwaite).

The Co-Parenting Era: Travis Scott and the Webster Children

Kylie's relationship with rapper Travis Scott (Jacques Bermon Webster II) is arguably her most significant due to the two children they share.

The On-Again, Off-Again Dynamic (2017–2023)

Kylie and Travis Scott were first linked in April 2017 after meeting at the Coachella music festival. Their relationship moved quickly, and within months, rumors of Kylie's first pregnancy began to circulate, though she kept the news private until after the birth.

The couple welcomed their first child, daughter Stormi Webster, on February 1, 2018.

After a temporary split in 2019, they reconciled during the COVID-19 pandemic and welcomed their second child, a son, on February 2, 2022. He was initially named Wolf Jacques Webster, but they later changed his name to Aire Webster.

Despite their enduring bond as co-parents, the couple's romantic relationship officially ended in late 2022/early 2023. Sources confirm that their focus remains on raising Stormi and Aire in a loving, blended environment, a common theme among the Kardashian-Jenner family.

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

The most recent and unexpected chapter in Kylie's dating history began in 2023, linking the beauty mogul with acclaimed actor Timothée Chalamet.

A Private Romance in the Public Eye

Rumors of a romance between Kylie Jenner and Timothée Chalamet first surfaced in April 2023, creating a massive media buzz due to the seemingly disparate nature of their public personas—a reality star/mogul and an Oscar-nominated indie film darling.

The couple maintained a high level of privacy for over a year, with rare public sightings and zero social media posts confirming their status. This private approach stood in stark contrast to Kylie’s previous relationships, which were often documented on *The Kardashians* (the family’s Hulu series) and her own social media channels.

The 2025 Red Carpet Debut

The relationship was officially cemented in the public sphere when the couple made their red carpet debut at the Met Gala in May 2025. This appearance confirmed that the relationship was serious and "on in 2025," despite persistent, though false, breakup reports that had circulated earlier in the year.

Sources close to the couple indicate that the romance is genuine and deep, with reports suggesting they are "really in love." Their relationship has continued to thrive throughout late 2025, with the pair reportedly spending major holidays together, prioritizing their connection away from the constant spotlight.

The pairing of the *Kylie Cosmetics* founder and the *Dune* actor has redefined what a celebrity relationship can look like in the modern era, balancing global fame with a fiercely guarded personal life. As of December 2025, the couple remains a strong, albeit private, unit, with fans eager for any glimpse into their ongoing romance.

kylie jenner relationships
kylie jenner relationships

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