The Ex-Files: A Deep Dive Into Kylie Jenner's Most Famous Former Boyfriends And Their Current Status

Kylie Jenner's romantic life has been a continuous source of global fascination, often playing out under the intense glare of the public eye. As of December 2025, the makeup mogul and reality star's past relationships remain a key part of her narrative, especially concerning the fathers of her children and the controversial romances from her younger years.

This article provides an in-depth, up-to-date look at the most significant ex-boyfriends in Kylie Jenner's life, detailing their history, their current status, and the lasting impact they’ve had on her life and career, focusing heavily on the latest updates regarding co-parenting dynamics and professional endeavors.

The Major Ex-Boyfriends: A Full Biography Profile

Kylie Jenner's dating history features two major, long-term relationships that defined distinct eras of her young adulthood: the controversial romance with rapper Tyga and the family-focused partnership with rapper Travis Scott. Here is a look at the men who shaped her public life.

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Travis Scott (Jacques Bermon Webster II)

• Full Name: Jacques Bermon Webster II
• Date of Birth: April 30, 1991
• Age: 34 (as of late 2025)
• Place of Birth: Houston, Texas, U.S.
• Profession: Rapper, singer, songwriter, record producer
• Relationship Timeline with Kylie: On-again, off-again from April 2017 to early 2023.
• Children with Kylie: Two: Stormi Webster (born 2018) and Aire Webster (born 2022).
• Notable Projects: Albums Astroworld and Utopia.

Tyga (Michael Ray Stevenson)

• Full Name: Michael Ray Stevenson (also known as Michael Ray Nguyen-Stevenson)
• Date of Birth: November 19, 1989
• Age: 36 (as of late 2025)
• Place of Birth: Compton, California, U.S.
• Profession: Rapper, singer, actor
• Relationship Timeline with Kylie: On-again, off-again from 2014 to April 2017.
• Children with Kylie: None.
• Notable Projects: Songs "Rack City," "Taste," and signing with Lil Wayne's Young Money Entertainment.

Travis Scott: The Co-Parenting Dynamic and Current Status

The relationship between Kylie Jenner and Travis Scott is arguably the most significant of her adult life due to the two children they share: daughter Stormi and son Aire.

The pair first met and began dating at the Coachella music festival in April 2017, shortly after her split from Tyga. Their whirlwind romance led to the birth of their first child, Stormi Webster, in February 2018.

A Focus on Successful Co-Parenting in 2025

While their romantic relationship officially ended for good in early 2023, the focus has entirely shifted to a healthy co-parenting partnership.

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Kylie has given rare insights into their current dynamic, stating that they are "doing the best job" they can to raise their children in a loving environment.

Sources close to the ex-couple confirm that their priority is maintaining a strong family unit for their two kids, even if the romance is over.

This commitment means they are often seen together at family events, holidays, and celebrations for Stormi and Aire, demonstrating a mature and amicable post-breakup relationship.

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Professionally, Travis Scott continues to be one of the biggest names in hip-hop, with his music and brand collaborations keeping him in the spotlight. His career remains a central focus, separate from his family life with Kylie.

Tyga: The Controversial Ex and His Current Career

Kylie Jenner's relationship with rapper Tyga was a defining, albeit controversial, chapter of her early fame. The on-again, off-again romance began when she was still a teenager, drawing significant media scrutiny due to their age gap.

The pair ultimately broke up in April 2017, just before Kylie began dating Travis Scott.

Tyga's Post-Breakup Perspective

In the years following their split, Tyga has occasionally spoken about the relationship, offering his perspective on why it ended. He suggested that the age gap and the differences in their backgrounds—Kylie's life in the Kardashian-Jenner reality TV world versus his music career—became too much.

He has also made claims about his influence on her early success, particularly regarding her initial rise in popularity and the launch of what would become the Kylie Cosmetics empire.

Despite the drama, Tyga has maintained that he will "for sure" always love her, indicating a lingering fondness for the reality star.

Tyga's Latest Professional Updates

As of 2025, Tyga is focused on his music career, continuing to release new tracks and collaborations. The rapper has successfully maintained his relevance in the music industry, moving past the intense media focus of his relationship with Kylie.

He continues to tour and release independent projects, cementing his status as a veteran in the rap game.

The Current Chapter: Moving Beyond the Exes

While her ex-boyfriends remain a constant topic of discussion—especially Travis Scott, due to their children—Kylie Jenner has clearly moved into a new phase of her life. The narrative around her has shifted from her teenage romances to her role as a mother, a successful businesswoman, and her current dating life.

Kylie Jenner and Timothée Chalamet

The most recent and high-profile development in Kylie's romantic life is her relationship with Oscar-nominated actor Timothée Chalamet. The pair have been linked since early 2023, creating a massive media buzz due to the unexpected nature of the pairing.

Despite persistent rumors of a split, the couple has made several high-profile public appearances, indirectly shutting down speculation about their relationship status.

Their joint appearances at major Hollywood events, sometimes even in matching outfits, signal that the relationship is serious and ongoing, marking a distinct departure from her previous relationships with fellow musicians.

This new romance, alongside her successful co-parenting with Travis Scott, shows Kylie's ability to compartmentalize her life, maintaining a healthy family dynamic while exploring new romantic connections outside of the "Kardashian bubble."

The Enduring Legacy of Her Relationships

The relationships with Tyga and Travis Scott have left an indelible mark on Kylie Jenner's brand. The Tyga romance was a catalyst for her transformation into a global figure, while the relationship with Travis Scott gave her the two most important people in her life: her children, Stormi and Aire. As she continues to evolve her career and personal life, her ex-boyfriends remain key figures in her story, forever linked by love, controversy, and co-parenting.