Kendall Jenner was branded a ‘rich b****’ and a ‘weird b****’ in a scathing new rant posted by the sister of one of her high-profile ex-boyfriends.
Earlier this week, Olivia Simmons — the sister of Kendall’s ex-boyfriend, NBA star Ben Simmons — shared a seemingly unprompted TikTok video recounting an awkward meet-up she and her brother allegedly had with the 29-year-old reality star.
In the video, Olivia — who also plays basketball like her brother — joked about Kendall’s allegedly poor baking skills after she tried to make a batch of cookies.
The Daily Mail has reached out to Kendall’s representative for comment but hasn’t yet received a response.
Without any explanation for her story, Olivia began by telling her fans: ‘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.”‘
Ben’s sister then brought up Kendall’s oft-mocked cucumber cutting technique.
Kendall Jenner was branded a ‘rich b****’ and a ‘weird b****’ in a scathing new rant posted by the sister of one of her high-profile ex-boyfriends, Ben Simmons; Jenner is pictured with Simmons in 2019 in NYC
Ben’s sister Olivia Simmons, who also plays basketball, shared a TikTok this week bashing Jenner for an awkward time when the reality star hung out with Simmons’ whole family
‘First of all, you’re Kendall Jenner. Don’t you guys have a chef?’ Olivia continued in the selfie video. ‘We saw you cutting up cucumbers, b****. You don’t know how to cook.’
Kendall was the butt of jokes on social media in 2022 after a clip of her trying to cook on her family’s reality series The Kardashians went viral.
During the episode, she turned down her mother Kris Jenner’s offer to have her chef make something to eat, and instead Kendall set about trying to cut up a cucumber, but she held the vegetable in a precarious, contorted manner that made many viewers question how much experience she had in the kitchen.
However, Simmons dated Jenner years before the awkward clip, so his sister couldn’t have had that context at the time.
In her TikTok video, Olivia noted that Kendall was only going to make cookies from ‘ready-made cookie dough,’ adding, ‘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.’
But according to Ben’s sister, the catwalk star was defeated even by the simplest baking task.
‘No, stop, because I have never seen so many uneven cookies. Like, what? What in tarnation?
She seemed to address Kendall directly then, saying, ‘You rich b****!
Olivia said Kendall wanted to make cookies, but Simmons’ sister mocked Kendall’s cooking because of a 2022 clip of her awkwardly cutting a cucumber — though that was years after the incident; Kendall pictured on The Kardashians
Kendall allegedly was making cookies from ready-made dough, but Olivia said, ‘I have never seen so many uneven cookies.’ She joked that Kendall should ‘call your f***ing chef to come and cook these cookies for you’
‘Anyway, it was just hilarious, because they’re just all — the Kardashians, the Jenners, like weird b****es,’ Olivia said, after previously calling Kendall a ‘rich b****’; seen Saturday in LA
‘If you don’t call your f***ing chef to come and cook these cookies for you…’ she said, before trailing off.
‘Anyway, it was just hilarious, because they’re just all — the Kardashians, the Jenners, like weird b****es.
‘And I know! I was sitting next to her!’ Olivia added emphatically just as the video ended.
Some fans in the comments were surprised at the personal jab, especially since it appeared to be unprompted.
‘I was ready for the tea and you served…poison??’ one commenter wrote.
‘weirdly mean for no reason,’ another user wrote, with another person adding, ‘This is so weird of you.’
‘You thought this ate,’ read one of the critical comments.
One fan who didn’t find the story funny wrote, ‘is the punchline in the room with us?’
Fans thought the exchange was unnecessarily mean and seemingly unprompted. Kendall and Ben dated from July 2018 to May 2019; pictured together in NYC
Simmons played for the Philadelphia 76ers from 2016–2022, then the Brooklyn Nets from 2022–2025. Nerve injuries ended his tenure in Brooklyn, but he then signed a one-year contract with the Los Angeles Clippers; pictured in February in Salt Lake City, Utah
‘Wait this is so mean for no reason! Why,’ echoed another user.
Several posters also though Olivia’s story was simply petty.
‘So she dated your brother and the most you can say is she made you uneven cookies ?! bye,’ wrote one user.
‘UNEVEN cookies had you, as a grown adult, bothered? Pls’ another commenter chastised her.
Jenner and Simmons were first linked back in the summer of 2018, confirming their relationship over the Fourth of July holiday. However, the two had split after less than a year, breaking up around May 2019.
Simmons, a point guard and power forward, played for the Philadelphia 76ers from 2016 to 2022, before taking up with the Brooklyn Nets that year.
However, his tenure with the Nets was plagued by nerve issues in his lower back, and his contract was bought out in 2025 by the team, before he moved to the Los Angeles Clippers.
Since ending his season with the Clippers, Simmons has remained a free agent.
