Keeping Up With Kendall Jenner’s Stacked Dating History

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Kendall Jenner isn’t really interested in having fans keep up with her love life.

Although she’s been incredibly famous since she was eleven – when she first appeared on Keeping Up With the Kardashians – that doesn’t mean everyone knows what she’s doing all the time.

Kendall Jenner is known for her active dating life, so much so that her sister Kim Kardashian once playfully wore a fan-made T-shirt referencing Kendall’s many rumored and actual boyfriends. The shirt, seen on an episode of The Kardashians in 2023, featured Kendall surrounded by photos of Blake Griffin, Ben Simmons, Jordan Clarkson, Kyle Kuzma, and Devin Booker.

But just because Kendall is huddled up with a guy doesn’t mean they’re endgame. 

In a 2017 interview with Harper’s Bazaar, she explained that she doesn’t share relationship details unless she’s completely sure about them. She asked, “Why would I share something with everyone else if I’m not fully invested, or even if I don’t understand it myself?”

Things appear to be going really well between her and actor Jacob Elordi. They were recently seen out with her sister Kylie Jenner and her boyfriend Timothée Chalamet on May 16th, and seemed very happy.

In 2023, the 30-year-old told WSJ. Magazine that they strive to find a healthy middle ground – protecting their personal life while still enjoying it, without letting outside pressures ruin things. They believe this approach is simply a better way to handle any relationship.

But once she’s in it, she’s all in.

In a 2023 interview with Harper’s Bazaar, she shared that she loves deeply and doesn’t apologize for it. She avoids saying goodbye whenever possible and always works to maintain her relationships. She’s felt this way since childhood, even though she used to be shy and reserved. Ultimately, she explained that she never gives up on anything.

You know, she explained it so well. Sometimes people just aren’t on the same wavelength, and they don’t want to connect deeply. But honestly, she’s totally okay with that! She’d much rather things stay open and give every opportunity a real shot, instead of closing herself off and wondering ‘what if?’ It really resonated with me – it’s a brave and optimistic way to look at things.

Let’s take a look at the men she’s dated, distinguishing between those she seriously pursued relationships with and those who were just brief interests.

When asked about her relationship with Harry Styles after they were seen having dinner together in West Hollywood in November 2013, Kendall Jenner told Giuliana Rancic that they were just friends. She described him as a “cool” guy.

Even after they were seen together in New York and London, Brody Jenner speculated that his half-sister was the one taking the lead in their relationship.

You know, when I spoke with him back in December, he seemed really optimistic about things. He told me she was clearly enjoying herself and that she’s incredibly grounded and mature for her age. Of course, he also pointed out that they’re both still very young, and navigating that can be tricky!

Kendall and Harry, who first connected as teenagers at ages 18 and 20, have remained in touch over the years. They were spotted together on several occasions, including a romantic yacht trip in 2016, and continued to reconnect in 2018 and 2020.

Even if nothing romantic developed, the two were sure to remain friends. There was speculation about a possible relationship as recently as 2022, after Harry ended his relationship with Olivia Wilde.

According to a source who spoke with TopMob News, she and Harry have always been just friends. They’ve stayed in touch and maintained a friendly relationship over the years.

Although Kendall Jenner and Justin Bieber were never officially a couple, they spent enough time together that rumors about a romantic relationship circulated.

Enough so that it was brought up during a Nightline interview Kendall gave in 2014.

She described the singer, known for his song ‘Baby,’ as a family friend. She added that people often jump to conclusions, but in this case, they’re wrong.

Kendall and Hailey Bieber have been close friends for a long time. When Kendall is dating someone, she often goes on double dates with Hailey and her husband, or she just hangs out with them as friends.

In August 2015, after his breakup, Nick Jonas was reportedly dating Kendall Jenner. His brother, Joe Jonas, and Joe’s girlfriend at the time, Gigi Hadid, had introduced them.

But they weren’t on the level of dating, according to Nick.

He told TopMob News that Kendall is wonderful and, because she’s close with Gigi and Gigi is dating Joe, they often find themselves in the same places and enjoy hanging out together.

In 2016, rumors swirled about a romantic connection between basketball player Jordan Clarkson, who was then with the Los Angeles Lakers, and Kendall Jenner, particularly around the Fourth of July. They appeared to still be dating when the NBA season began in November.

Jordan attended Kendall’s lavish 21st birthday party that month, but they didn’t become anything more than acquaintances.

Also on Kendall’s radar at the time, at least as a cool guy to hang out with, was A$AP Rocky.

He seemed to be waiting for Rihanna to be interested in him, but he enjoyed spending time with Kendall Jenner in 2016 and 2017. They went on dates, partied in cities like Miami and New York, attended Coachella together, and even posed for Kylie Jenner’s famous Met Gala selfie.

Starting in August 2017, Kendall Jenner was frequently seen out and about with Blake Griffin, who was then playing for the L.A. Clippers. She also attended several of his games, sitting courtside.

It was fun spending time together, but it never really turned into a serious relationship. Then, in 2018, Blake was traded to the Detroit Pistons, and that ended things.

Ben Simmons and Kendall Jenner started dating in the spring of 2018. They made an effort to see each other whenever they could, even though Simmons was playing basketball in Philadelphia.

I remember reading about this – it was so cool! Back in spring 2019, Kendall was doing a photoshoot with Australian Vogue, and she actually paused to stream a 76ers game! But the best part? She FaceTimed Ben Simmons, who’s from Melbourne, to show him her copy of his recent GQ Australia cover. It was such a sweet moment and really showed their connection.

I cherish my close relationships and friendships, and I prefer to keep them private,” the model explained to Australian Vogue. “I’m still young, and I don’t think relationships are always straightforward at this point in my life.

By the first Monday in May 2019, the date of the Met Gala, Kendall and her partner had already broken up, with Kendall anticipating her busy work life would create difficulties in the relationship.

In an interview with Australian Vogue, she explained that everyone finds their own way in life, and it’s okay to make mistakes in your twenties as you learn and grow.

By 2019, people online had noticed a trend. A fan created a meme showing a starting five NBA lineup of players Kendall Jenner had reportedly dated: Jordan Clarkson, Ben Simmons, Blake Griffin, Kyle Kuzma (then with the Lakers), and D’Angelo Russell.

“This is a playoff team lmao,” the fan wrote.

Then it was Kendall with the dunk: She reposted, adding, “2 out of 5 accurate, thanks.”

From 2020 to 2022, Kendall Jenner dated basketball player Devin Booker. Their relationship lasted almost two years, and he even accompanied her to her sister Kourtney Kardashian’s wedding in Italy in May 2022.

However, just a month later, they began spending time apart. A source told TopMob News that after returning from their trip, they realized they weren’t compatible and had very different ways of living.

Things heated up again in July, but by November, they were drifting apart due to conflicting schedules. Interestingly, before Kim Kardashian even had a T-shirt made of the meme, he had replaced D’Angelo in the popular online lineup.

A recent sighting of the couple, wearing snow goggles and spotted together at a restaurant in Aspen over Valentine’s Day weekend in 2025, suggests they’re embracing the idea that your twenties are a time for exploration and figuring things out as you go.

Bad Bunny and Kendall Jenner started dating in 2023. They were first seen together in February, on what looked like a double date with Justin and Hailey Bieber.

Kendall first saw the Puerto Rican artist perform at Coachella in April. The next month, they were seen together at a Met Gala afterparty and later at a Lakers game, even coordinating their outfits.

They continued to go on dates for several months, even attending a Gucci fashion show in Milan that September. However, their relationship ended before the year was out.

Since they were able to remain friends, the pair – who share many common acquaintances – have gotten back together on several occasions, in various places around the globe.

Bad Bunny snagged a front-row seat at New York Fashion Week in February to watch Kendall Jenner model for Calvin Klein’s Autumn/Winter 2025 show.

Recent reports suggest things are going really well between Kendall and Jacob Elordi, the actor from Euphoria.

On May 16, 2026, she was seen with an Oscar nominee in Los Angeles, along with Kendall Jenner’s sister, Kylie, and Kylie’s boyfriend, Timothée Chalamet. This followed another sighting of the pair enjoying time in Hawaii.

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2026-05-19 21:18