Kylie Jenner Boyfriend has become one of the most recognized names in the world, not only for her groundbreaking success in beauty and business but also for her high-profile love life. From her teenage years to her current romance with Hollywood star Timothée Chalamet, Kylie’s dating history has fascinated fans and media alike. Every relationship has captured attention for different reasons, whether it was her first long-term romance, the birth of her children, or the glamour of celebrity partnerships. In this article, we explore Kylie Jenner’s boyfriend history, offering a complete, detailed look at her relationships, her approach to love, and how she balances dating with motherhood and career.
Quick Bio Information
Name: Kylie Jenner
Date of Birth: August 10, 1997
Place of Birth: Los Angeles, California, USA
Occupation: Reality Star, Entrepreneur, Founder of Kylie Cosmetics
Family: Kris Jenner (Mother), Caitlyn Jenner (Parent), Kendall Jenner (Sister)
Children: Stormi Webster (Daughter), Aire Webster (Son)
First Public Relationship: Tyga (2014–2017)
Notable Partner: Travis Scott (2017–2023)
Current Partner: Timothée Chalamet (2023–Present)
Height: 5’6” (168 cm)
Net Worth: Estimated $1.2 Billion
Business Ventures: Kylie Cosmetics, Kylie Skin
Social Media Followers: Millions across Instagram, Twitter
Public Image: Influential Celebrity, Fashion Icon, Entrepreneur
Awards: Various beauty and business accolades
Philanthropy: Involved in charitable activities through family foundations
Early Rumors and Teenage Flings
Before Kylie became a global business mogul, her teenage years were already in the public eye. During this time, she was rumored to have dated several young stars, though many of these relationships were more speculation than confirmed romances. Among the earliest rumors was Australian singer Cody Simpson, with whom Kylie was photographed sharing affectionate moments in 2011. While neither of them confirmed a relationship at the time, Cody later reflected on the brief connection with humor, suggesting it was more of a casual teenage fling.
Another name often linked to Kylie during her teen years was Jaden Smith. The pair were close friends, sharing trips and public appearances, including attending awards shows together. While Kylie never officially confirmed a romantic relationship, her birthday posts for Jaden highlighted their closeness. These early experiences with high-profile peers helped shape Kylie’s understanding of public relationships, even before her first major romance.
First Major Romance: Tyga
Kylie Jenner’s first long-term relationship was with rapper Tyga, a romance that began when she was 17. The pair initially met at Kendall Jenner’s birthday party in 2011, but their relationship did not officially start until 2014. Tyga, who was seven years older, had just ended his engagement to Blac Chyna, which added a layer of public intrigue to their connection.
The relationship was marked by on-and-off periods over almost three years. Tyga famously gifted Kylie a $320,000 Ferrari for her 18th birthday and even got a tattoo dedicated to her. Kylie appeared in Tyga’s music video for the song “Stimulated,” which fueled media speculation that the lyrics were about her. Despite the ups and downs, Kylie later reflected on the relationship positively, emphasizing that there were no major conflicts and that they would always share a bond.
Travis Scott: The Father of Her Children
After her split from Tyga in 2017, Kylie Jenner began dating Travis Scott, born Jacques Bermon Webster II. The pair were first publicly spotted together at Coachella in 2017, sparking immediate interest in their romance. Their connection quickly became serious, and by September of that year, Kylie was reportedly pregnant with their first child.
In February 2018, the couple welcomed daughter Stormi Webster, marking a turning point in Kylie’s life as she embraced both motherhood and fame. She appeared alongside Travis in Playboy’s “Pleasure Issue”, where she spoke openly about how sexuality and motherhood could coexist. In 2022, they welcomed their second child, a son originally named Wolf, later introduced as Aire. While their relationship was deeply passionate, it was also on-and-off, with the pair ultimately splitting less than a year after their son’s birth. Despite the challenges, the couple has maintained a co-parenting relationship, prioritizing their children’s wellbeing above all else.
Brief Rumors and Friendships: Drake and Others
Kylie’s dating life has occasionally included high-profile rumors. After her 2019 split from Travis Scott, she was reportedly spending time with rapper Drake. The pair had been family friends for years, and sources suggested they were “flirting and hanging out” during Kylie’s time apart from Travis. While some insiders insisted they were “just friends,” their social interactions and appearances at Drake’s events fueled speculation. These brief rumored flings demonstrate how Kylie’s social circle and fame often lead to public curiosity about her love life, even when relationships are casual.
Current Relationship: Timothée Chalamet
In 2023, Kylie Jenner began spending time with actor Timothée Chalamet, sparking new waves of media attention. Reports revealed that the pair were casually dating and “getting to know each other,” often meeting weekly and enjoying a lighthearted, pressure-free romance. Public sightings, including Paris Fashion Week and a Beyoncé concert, showed them sharing affectionate moments and enjoying their time together.
Sources close to Kylie described the relationship as fun and easygoing, emphasizing that she is focused on enjoying life without the stress of intense public scrutiny. Timothée has reportedly impressed Kylie with his presence and mindset, reminding her to live in the moment. Her family, especially Kris Jenner and Kim Kardashian, have been supportive of the relationship, which is seen as promising yet relaxed.
How Kylie Balances Dating and Motherhood
One of the most remarkable aspects of Kylie Jenner’s personal life is how she manages her relationships alongside motherhood and her thriving business ventures. Whether dating Tyga, Travis Scott, or Timothée Chalamet, Kylie has consistently emphasized that her children are her top priority. She maintains a careful balance, choosing partners who understand her commitments and values.
Kylie’s approach reflects a modern perspective on parenting and dating, showing that it is possible to maintain romantic connections while being deeply involved in family life. Her focus on quality over quantity in relationships ensures she remains grounded while navigating public attention.
Patterns and Lessons in Kylie Jenner’s Relationships
Looking across Kylie Jenner’s dating history, several patterns emerge. She tends to date high-profile celebrities, particularly those in music or entertainment, which aligns with her social and professional circle. Many of her relationships have been on-again-off-again, often influenced by lifestyle differences, media pressure, or personal growth.
These experiences have shaped Kylie’s approach to love, teaching her the importance of compatibility, communication, and prioritizing personal happiness. Her public journey offers insights into the challenges and rewards of dating while living under intense scrutiny.
Public and Media Reactions
Kylie Jenner’s relationships have always attracted media and fan attention. From Tyga’s tattoo dedications to Travis Scott’s red carpet appearances with Kylie, each romance has been documented and discussed widely. Public reactions range from support and excitement to speculation and controversy.
The media’s constant coverage has influenced how Kylie presents herself in relationships, often encouraging privacy during significant life events, like the birth of her children, while sharing carefully curated glimpses of her personal life.
Kylie Jenner’s Dating Philosophy Today
Today, Kylie Jenner’s dating philosophy appears to be focused on balance and enjoyment. She enjoys dating casually, as seen with Timothée Chalamet, while ensuring her children and career remain central. She prioritizes emotional compatibility and shared values over public attention or media approval.
Kylie has publicly spoken about the importance of maintaining independence and self-awareness in relationships, which allows her to navigate love in a way that is authentic, mature, and sustainable.
Complete Timeline of Kylie Jenner’s Boyfriends
Kylie Jenner’s dating journey can be summarized in a timeline that highlights her growth and evolution in relationships:
2011 – Cody Simpson (Rumored Teenage Romance)
2013 – Jaden Smith (Close Friendship, Speculated Flirtation)
2014–2017 – Tyga (First Long-Term Relationship)
2017–2023 – Travis Scott (Father of Stormi and Aire)
2019 – Drake (Rumored Flirtation, Just Friends)
2023–Present – Timothée Chalamet (Current Casual Relationship)
This timeline shows how Kylie has navigated different stages of life, from adolescence to adult relationships, while managing public attention and personal growth.
Final Thoughts
Kylie Jenner’s dating history offers more than celebrity gossip; it reflects her personal growth, evolving priorities, and resilience under public scrutiny. From early teenage flings to major relationships with Tyga and Travis Scott, and now a promising romance with Timothée Chalamet, Kylie’s journey illustrates how love, family, and career can coexist with maturity and balance. By navigating her personal life thoughtfully, Kylie continues to inspire fans not only as a business icon but also as someone who manages love and motherhood with grace.
Her story shows that behind the headlines and social media buzz, there is a young woman learning, growing, and making deliberate choices about her relationships, offering a model for modern love in the public eye.
FAQs About Kylie Jenner Boyfriend
Who Was Kylie Jenner’s First Boyfriend?
Kylie’s first notable public relationship was with rapper Tyga, which began in 2014 when she was 17. The relationship lasted almost three years and received significant media attention.
Who Is Kylie Jenner Dating Now?
As of 2025, Kylie Jenner is reportedly dating actor Timothée Chalamet. The relationship is described as casual, fun, and supported by her family.
How Many Children Does Kylie Jenner Have?
Kylie has two children with Travis Scott: daughter Stormi, born in 2018, and son Aire, born in 2022.
Did Kylie Jenner Date Drake?
After her split from Travis Scott in 2019, Kylie was rumored to be spending time with Drake. However, insiders have stated that they were mostly friends.
What Is Kylie Jenner’s Approach to Dating?
Kylie prioritizes her children, career, and personal happiness. She enjoys dating casually but looks for emotional compatibility and shared values.
Who Was Kylie Jenner’s Most High-Profile Relationship?
While Kylie has had several celebrity partners, her relationship with Travis Scott stands out due to the birth of her children and extensive public interest.
Has Kylie Jenner Dated Outside the Entertainment Industry?
Most of Kylie’s relationships have been with high-profile figures in music and entertainment, aligning with her social and professional circles.
How Has Kylie Jenner’s Dating Life Evolved?
Kylie has matured from teenage flings and early celebrity romances to a more thoughtful, balanced approach focused on family, happiness, and sustainable relationships.
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