Kylie Jenner and her boyfriend: Step inside intriguing history of model’s dating


Kylie Jenner, a member of the famous Kardashian-Jenner clan, is not just known for her beauty and business acumen but also for her intriguing dating history. The reality TV star and business mogul has had her fair share of high-profile relationships that have captivated the media and her fans. In this article, we will take a closer look at some of the key milestones in Kylie’s dating history.

  1. Jaden Smith (2013)

Kylie’s dating history began to make headlines in 2013 when she was linked with Jaden Smith, the talented son of actor Will Smith. Although their relationship was never officially confirmed, the two were often seen together and seemed quite close. This teenage romance was short-lived but left a lasting impression on fans.


Kylie Jenner & Jaden Smith leaving a movie theater with her foundation all  over his face, 2013 : r/popculturechat
image credits: Reddit
  1. Tyga (2014-2017)

The business mogul most talked-about relationship was with rapper Tyga. The couple went public with their romance in 2015, sparking a lot of controversy due to their age difference, with Kylie being underage at the time. Despite the initial backlash, the two were together for several years, even briefly getting engaged. Their relationship eventually ended in 2017.

Kylie Jenner and Tyga's Relationship: A Look Back
image credits: PEOPLE
  1. Travis Scott (2017-2022)

Kylie’s most high-profile and enduring relationship has been with rapper Travis Scott. The couple began dating in 2017, and their relationship quickly became the talk of the town. In February 2018, they welcomed their first child, Stormi Webster, and have been co-parenting successfully, even after their brief split in 2019.

However, they had their on-again-off-again going for quiet a while. In May 2021, the cosmetic entrepreneur confirmed that she had rekindled her romance with Travis. A few months later, Page Six had reported the couple is pregnant with their second baby. They welcomed baby boy in February.

Kylie Jenner Reveals Where She & Ex Travis Scott Stand as Co-Parents
image credits: E! Online
  1. Timothee Chalamet

The model was first linked with Timothee Chalamet when in April 2023 when her luxury Range Rover was snapped in the actor’s driveway. Sources had claimed that the two have been dating and Kylie has been finding it really fun.

Sometime later, the pair were spotted making out at the US Open. Kylie proved that she was all in for Timothee when she accidentally confirmed that he was her iPhone background.

The couple went all public when the attended Beyonce’s Renaissance Tour together and did not shy away from putting on a show with their PDA.

Kylie Jenner and Timothée Chalamet's PDA Moment at the US OpenAs Kylie Jenner and Timothee Chalamet shock fans by confirming their  romance with a PDA-packed display at Beyonce - who are the other unexpected  relationships of the year? | Daily Mail Online
image courtesy: Cosmopolitan, Daily Mail
  1. Other Rumors

Kylie’s dating history has also included a few rumored relationships, with one of the most notable being Fai Khadra, a Palestinian-American model and musician. The two have been close friends for a long time, which has sparked dating rumors on several occasions, although nothing has been officially confirmed.

Over the years, the 26-year-old has been linked to various other celebrities, including A$AP Rocky and Drake, though these relationships have not been officially confirmed, and the rumors have often been fueled by speculation and the media’s watchful eye.

Kylie Jenner’s dating history has been a rollercoaster ride of high-profile romances, rumors, and public scrutiny. Through it all, she has managed to maintain her status as a successful entrepreneur and influencer. While many aspects of her personal life have been the subject of intense media speculation, it’s essential to remember that celebrities, like anyone else, have their ups and downs in relationships. Kylie’s story is a reminder that, despite her fame, she is just like anyone else when it comes to matters of the heart.