Exploring Kendall Jenner’s Dating History: Everything We Know About The Supermodel’s Love Life

As I delve into the romantic journey of Kendall Jenner, a modern-day Cinderella of sorts, it’s fascinating to see how her love life has mirrored the ebb and flow of the tides. From the enigmatic Ben Simmons to the charismatic Devin Booker, each relationship offers a unique insight into Kendall’s evolving perspective on love and relationships.

Discussions about Kendall Jenner’s romantic relationships have been frequent. Despite the fact that celebrities are known for living their lives in the spotlight, providing content for media outlets and keeping fans interested, Kendall’s private life tends to be kept more discreet.

The Kardashian-Jenner sisters exist in a world all their own, with numerous brand deals, investments, and their own reality TV series. They constantly remain under the public eye, and regardless of whether one admires them or dislikes them, they are impossible to overlook.

Unlike most members of the Kardashian family who thrive on public attention and scandal, model Kendall Jenner tends to keep her private and romantic affairs under wraps, preferring instead to let her professional accomplishments speak for themselves.

2021 saw Farnaz Farjam, producer of Keeping Up with the Kardashians, shed light on Kendall Jenner’s dating habits. As per Farjam, Kendall follows a private rule of dating someone for at least a year before making them part of her show’s narrative, which is why her personal life remained off-screen.

Over the course of her career, the supermodel’s name has been associated with various high-profile individuals, ranging from musicians like Harry Styles to rappers such as Bad Bunny. We will delve into some of these connections shortly. It is worth noting that, much like her older sisters, Jenner has a history of dating athletes. As a result, her romantic past appears to be quite extensively chronicled.

Let’s delve into Kendall Jenner’s romantic journey from 2013 up till the present. Feel free to take a break and get yourself a bite to eat, as this is quite an extensive yet entertaining read!

1. Harry Styles ( 2013)

Following his split with Taylor Swift in 2013, Harry Styles was observed on his initial date with Jenner in November. Initially, a source stated that they were just friends to PEOPLE, but by January 2014, their relationship appeared more serious. They seemed to have a friendship and an off-and-on romantic connection for several years. They were spotted together again on New Year’s Eve in 2015, celebrating the new year on a private yacht in St. Barts.

It’s clear that there was a strong sense of romantic interest and affection, as well as plenty of physical interactions, between the two of them. They have been seen together on multiple occasions.

In 2017, Styles launched his first studio album. Fans speculated that he was referring to Jenner during an interview with Rolling Stone when discussing a previous relationship as his creative inspiration. “She plays a significant role in the album,” he stated about this mysterious source of inspiration.

From my perspective as a lifestyle enthusiast, it appears they’ve maintained a cordial relationship, though they’ve kept their interactions relatively private. Intriguingly, in 2022, I found myself at one of his concerts – a performance that seemed to subtly reference both Kylie Jenner, a member of the Jenner clan, and Hailey Bieber, a friend.

2. Nick Jonas ( 2015)

Nick Jonas, who is well-known as the most recognized member of the Jonas Brothers family, got acquainted with Kendall Jenner through Joe Jonas and his then-partner Gigi Hadid. Not long ago, Nick had parted ways with his girlfriend Olivia Culpo. According to sources, their communication with Jenner showed a playful chemistry right from the beginning.

As a bachelor on the hunt for romance, it’s uncertain if there was an immediate spark between them. However, according to ELLE magazine, Nick couldn’t help but find the supermodel incredibly attractive.

Nevertheless, their relationship didn’t seem to advance much. Now, Jonas is happily married to the renowned Indian actress Priyanka Chopra, and they recently became parents through surrogacy.

3. Jordan Clarkson (2016)

Jenner and NBA player Jordan Clarkson were first seen together in March 2016. According to a source who spoke with PEOPLE in April 2016, they maintain a low profile when they’re out in public, but they are very much a couple behind closed doors, showing affection towards each other. The source added that Clarkson is quite smitten by her.

Due to their high-profile status, it was evident that a strong romantic chemistry existed between the two celebrities. According to PEOPLE magazine, they were rumored to be a couple and even celebrated Kylie Jenner’s 22nd birthday together. Additionally, they were spotted attending rapper Drake’s American Music Awards afterparty.

However, things seemed to have naturally ended shortly after a while.

4. A$AP Rocky ( 2016-2017)

For quite some time, rappers A$AP Rocky and Jenner have been close companions. However, neither of them ever officially confirmed if their relationship extended beyond friendship. Still, this didn’t deter fans from generating theories. The first instance where they were observed together was in Paris during June 2016, strolling towards one of Jenner’s favorite eateries, L’Avenue. A couple of months later, in October, they were both seen entering a hotel in Los Angeles together.

In March 2017, a friend revealed to PEOPLE that they had been spending a significant amount of time together, and the model was receptive to exploring where their relationship might lead. The following month, she attended A$AP’s Coachella performance, and spectators observed them being very affectionate at an afterparty.

Initially, they were often seen together, but over time their appearances as a duo became less frequent. Nowadays, Rocky can be found alongside pop sensation Rihanna; they are parents to two children together.

5. Blake Griffin ( 2017-2018)

In the summer following her Met Gala with the rapper, sources say Kylie Jenner was spotted with NBA player Blake Griffin on numerous occasions. According to PEOPLE, their relationship wasn’t serious; she had been spending a lot of time in LA and was simply enjoying herself. The source stressed that she was just having fun at the moment.

By autumn 2017, she along with Griffin attended Halloween Horror Nights and cheered for him at a Clippers match. According to People magazine, they seemed content as a couple.

Back in March 2018, she denied being in a relationship with Griffin. Later on, it was reported that the reason for their separation was due to Griffin having to go abroad for his sport, which created a long-distance situation between them.

6. Ben Simmons ( 2018-2019)

In May of 2018, rumors started swirling about Caitlyn Jenner and basketball player Ben Simmons. At first, their relationship was up-and-down and it took some time for them to officially become a couple. However, in February 2019, Caitlyn publicly acknowledged the relationship on The Ellen DeGeneres Show.

Ellen DeGeneres asked, “It seems clear that you’re dating someone from the 76ers. How long has this relationship been going on?” Jenner responded with a shy smile, saying, “We’ve been together for some time now.”

Jenner had suggested the prospect of marriage during an interview with Vogue Australia back in May 2019, yet their relationship ultimately took a pause, as confirmed by a source familiar with them to PEOPLE. “The bond between them reached its natural conclusion.”

The two still seem to keep it cool and are on good terms even today.

7. Devin Booker( 2020-2022)

Kendall Jenner and basketball player Devin Booker from the Phoenix Suns initially fueled dating speculation in April 2020, as they were observed traveling together to Arizona. A source shared with PEOPLE back then that Kendall appeared quite content.

As a longtime social media user, I can attest to the power of platforms like Instagram in capturing and sharing significant moments in our lives. Last Valentine’s Day was no exception for Jenner, who used her account to commemorate an important milestone – one year with her partner. The couple marked the occasion by flooding their followers’ feeds with a heartwarming series of PDA-filled posts that made me smile and feel the love radiating from my screen. It was a sweet reminder of the joy that can be found in celebrating our relationships, even amidst the hustle and bustle of everyday life.

After September 2022, the deeply affectionate couple parted ways due to their hectic work schedules and professional commitments.

Later on, they shared with PEOPLE that they hold a deep affection and regard for one another, hoping for nothing but the best.

8. Bad Bunny

Jenner and Bad Bunny had been in a romantic relationship for approximately ten months before they apparently parted ways in December 2023. The announcement of their breakup made headlines following reports that they spent Thanksgiving separately. Additionally, it was reported that Jenner traveled to Aspen, Colorado, with a group of girls during the middle of December without him.

The pair reportedly spent time together at the same hotel during the post-event, seated at the same table. They were seen laughing and showing affection, indicating a playful rapport. Although earlier reports suggested their relationship was casual and led to some difficulties, causing them to split up, they rekindled their connection in 2023. As stated by PEOPLE, they admitted missing one another and decided to give their relationship another chance.

The duo enjoyed their summer vacation as a pair, announcing their relationship publicly in September. They also appeared in a Gucci luggage advertisement. Although it is not definitively confirmed at this point if they are still an item, many gossip magazines suggest that they remain together.

Prior to dating Kendall Jenner, Bad Bunny had been in a prolonged romance with Gabriela Berlinger from 2017 to 2022. His longest-known relationship was with Carliz De la Cruz, which lasted for five years before they separated in April 2017.

2024-08-19 15:40