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Kendall Jenner Roasted by Ex Ben Simmons’ Sister in Scathing Video: 'Weird B----'

Photo of Kendall Jenner, Ben Simmons and Olivia Simmons
Source: MEGA/@livvyschannel/TikTok

Kendall Jenner got dragged by ex Ben Simmons' sister Olivia in a shocking TikTok confession.

Oct. 21 2025, Published 5:58 p.m. ET

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NBA star Ben Simmons’ sister Olivia Simmons dragged Kendall Jenner in a ruthless TikTok.

Olivia shaded the reality star, 29, and had some choice words for the rest of her family.

Ben and Kendall dated on and off between May 2018 and May 2019.

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Source: @livvyschannel/TikTok

Olivia Simmons unexpectedly dragged Kendall Jenner online.

“So my brother used to date Kendall Jenner, and I will never forget the time we — as a family — were sitting around playing Cards Against Humanity, and she was like, ‘I’m gonna bake some cookies,'” Olivia started her video. “First of all, you’re Kendall Jenner. Don’t you guys have a chef? We saw you cutting up cucumbers, b----. You don’t know how to cook.”

Olivia was referring to a viral video of the odd way Kendall cut cucumbers on a 2022 episode of The Kardashians.

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Image of Kendall Jenner and Ben Simmons started seeing each other in May 2018.
Source: @kendalljenner/Instagram

Kendall Jenner and Ben Simmons started seeing each other in May 2018.

While they were hanging out, Kendall opted for “ready-made cookie dough.”

“You really don’t have to do much but, like, put it in the right place at the right time. Like, the only thing that you need to do is chop them up evenly,” Olivia quipped. “I have never seen so many uneven cookies. … What in tarnation?”

She then went on to address the Victoria’s Secret Angel directly: “You rich b----. If you don’t call your f------ chef to come and cook these cookies for you?”

Olivia concluded, “Anyways, it was just hilarious because the Kardashians, the Jenners, they’re just, like, weird b------.”

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Kendall Jenner

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Image of Kendall Jenner dated Ben Simmons.
Source: MEGA

Kendall Jenner dated Ben Simmons.

She tagged Kendall in the caption of her TikTok, writing, “Cause girl we seen that cucumber video what the HELLY……… call the chef please cause the cookies were terrible 😂😂😂😂😂😂.”

Fans were confused as to why Olivia felt the need to share the story about Kendall at this point in time.

“I don’t get the purpose of this story??” one person questioned, while another mocked her, “You thought this ate 😂.”

Several users deemed the recollection “unnecessary” and called Olivia “weirdly mean for no reason.”

Image of Kendall Jenner reportedly split from Ben Simmons in May 2019.
Source: @kendalljenner/Instagram

Kendall Jenner reportedly split from Ben Simmons in May 2019.

Dating rumors first sparked between Ben and Kendall in 2018, when they were spotted on a lunch date at the Beverly Hills Hotel in California. They later hung out in New York with a group of friends at the now-closed restaurant Vandal.

“Security measures seemed to have been taken to ensure Kendall and Ben enjoyed their night hassle free,” an eyewitness dished at the time. “They were smiling the night away with their friends.”

The exes were videoed cuddling in the background of Khloé Kardashian’s Fourth of July Instagram post that summer.

In May 2019, an insider confirmed “the relationship ran its course.”

“She’s spending time with her friends and back to being in fun mode,” the source added.

Though there were rumors they linked back up again in 2020, the gossip was never confirmed.

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