Celebrities Dated Kendall Jenner Hailey Baldwin, Supermodel Best Friends

Kendall Jenner & Hailey Baldwin are close friends. Like… really close. You can tell by the way the 22-year-old brunette & 21-year-old blonde are always attached at the hip, usually with their fellow models on vacation. In fact, they’re SO close, they even seem to share their boyfriends!

This week, while taking a look at Justin Bieber‘s new fiancée‘s dating timeline, we couldn’t help but notice how familiar the names on Hailey’s list are… We realized it’s because more than half of them are also on Kendall’s dating timeline, too!

Justin Bieber

Justin Bieber is a big fan of the Kardashian-Jenner clan. So much so, he’s been linked to Kourtney Kardashian, as well as Kendall & Kylie Jenner. Blech. But, today, we’re talking about his supposed relationship with Kenny.

Though JB’s ex, Selena Gomez, seemed to be all buddy-buddy with the Jenner sisters around Coachella 2014, all of a sudden, she unfollowed the pair on social media. According to reports, Justin hooked up with Kendall — and Selena caught them in the act!

Rumors of something more than friendship between Justin and Kendall persisted throughout 2015, especially after he posted this PDA-packed picture on Instagram that April. It was “never serious” with Kenny, though, the Biebs revealed in an interview with Billboard that November.

In that same Billboard interview, Justin called Hailey one of his “best friends in the entire world.” And that friendship soon skyrocketed to best friends with benefits, as he posted a hot-and-heavy makeout picture with the supermodel on January 6, 2016.

Their relationship was on and off after that, but now it seems like the two are aiming for it to be permanently ON, as they reportedly got engaged over the weekend.


Kendall’s family members have been friends with Drake for a long time, so it’s not usually suspicious to see the two of them together. However, in January 2015, relationship rumors circulated. According to Daily Mail, “the model went one step towards fueling rumors that she and “Take Care” singer Drake were dating when she left the same restaurant minutes ahead of him, looking coy as she exited with her head down.”

Nearly a year later, in December 2015, the rapper posted this picture of himself with making a funny face next to the supermodel, who was making a kissy face to the camera, further sparking the buzz.

By the time Memorial Day came around the following year, he was spotted getting cozy with KJ’s BFF, HB. TMZ reported that “Drake and Hailey slipped into The Nice Guy Tuesday around 11:30 PM and got a table with another couple. We’re told the table ordered shots — and while you can see Hailey spent some time staring into her phone… she and Drake were cozy enough that it was clear they were on a date.”

“Drake even pulled the move — y’know… arm behind her on the sofa,” the report continued. “They pulled that other move when they left around 2:30 AM — she went out the front, Drake took the back door.”

Ashton Irwin

The same year Kendall may or may not have been involved with Justin’s 2014 rift with Selena, she may or may not have been involved with 5 Seconds of Summer‘s Ashton Irwin.

That August, the pair was spotted getting into a taxi in NYC after hanging out with 5SOS bandmate Calum Hood, pals Nicole & Danielle Kahlani… and Hailey Baldwin. But, recently, Ashton hinted to in a hit105 interview (via Daily Mail) that it may’ve all been a setup for the paparazzi, saying that “some people might want you to be seen with a certain person.”

He continued to say that he hasn’t “spoken to Kendall in a minute… we weren’t doing…” before trailing off.

More than two years after Ashton & Kendall grabbed a cab together, he was spotted out and about with Kenny’s BFF, Hailey. In early November 2016, they were pictured walking in Los Angeles, leading people to, naturally, suspect a relationship between them. TMZ followed up on the rumors a couple weeks after the duo’s LA ~date~, but Ashton shot them down. “Hailey Baldwin is a very close friend of mine. She’s a wonderful woman,” he said, before admitting, “I’m not dating her.”

Lewis Hamilton

Lewis Hamilton definitely has a type: models. The 33-year-old Formula One World Champion has been linked to a slew of them, including Gigi Hadid, Barbara Palvin, Sofia Richie and Winnie Harlow. Oh, and Kendall & Hailey, duh!

Lewis was first rumored to be hooking up with KJ in May 2015, when she was spotted wearing his chain in a group photo while at one of his races. Four months later, the two were seen walking together during New York Fashion Week, leading to more relationship rumors.

The Lewis-Hailey relationship rumors began about a half a year later, in February 2016 — one more after THAT kiss with Justin Bieber — when they showed up together at Elton John‘s Oscars viewing party. They even posed with their arms wrapped around each other on the red carpet.

Jordan Clarkson

Like Lewis Hamilton, NBA star Jordan Clarkson also loves to date models. He was previously linked to Bella Hadid, Chanel Iman and, of course, the two beautiful supermodels in question, Kendall and Hailey.

The Cleveland Cavaliers player and brunette beauty were said to be “casually dating” in July 2016, after they were spotted ringing in Independence Day in Malibu together.

Awkwardly, the first time Hailey and Jordan were linked was on New Year’s Eve 2016, when he definitely still had SOMETHING going on with Kendall. There’s photographic evidence that Hailey and Jordan held hands that night — the same night he was seen making out with Kendall!

A year later, in December 2017, he was spotted in Hailey’s company again… with Bella Hadid… whom he was linked to the following month! Man, these supermodel BFFs sure are incestuous.

Chandler Parsons

Another NBA star with connections to Kendall & Hailey is Memphis Grizzlies player Chandler Parsons.

The first time Kendall and Chandler were romantically linked was in August 2014. According to Daily Mail, Kris Jenner is the one who set them up! “Mama Kris met Chandler a few weeks ago and was blown away by not only his good looks, but his promising B-ball future,” the site boasted.

Dating rumors were sparked, once more, in January 2017, after they were caught in each other’s company more than once within a week. However, it was right after she locked lips with Jordan on NYE, so…

The Hailey-Chandler dating rumors started around the same time (like, literally the same day), but Hailey denied the claims. And yet, that August, Hailey & Chandler were spotted on a double date with Kendall and her boyfriend from 2017-2018, Blake Griffin.

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