Originally appeared on E! Online
Ben Simmons‘ sister just took a shot at Kendall Jenner‘s cooking from down town.
Olivia “Liv” Simmons poked fun at the Los Angeles Clippers player’s former girlfrienddetailing her lack of skills in the kitchen.
“I will never forget the time we were all, as a family, we were all sitting together playing Cards Against Humanity,” Liv said on her TikTok on Oct. 18 before launching into a mock impression of the Kardashians star, “and she was like, ‘I’m gonna bake some cookies.'”
“First of all,” Liv continued, rolling her eyes, “you’re Kendall Jenner. Don’t you guys have a chef? We saw you cutting up cucumbers. You don’t know how to cook.”
The 29-year-old, who went viral for awkwardly cutting the fruit on season two of The Kardashians—used ready-made cookie dough. And even then ran into some difficulty.
“You don’t really have to do much but put it in the right place at the right time. The only thing that you need to do is chop them up evenly,” Liv explained. “No, stop, because I have never seen so many uneven cookies. Like, what? What in tarnation? You rich b—h. If you don’t call your f–king chef to come and cook these cookies for you?'”
Liv threw even more shade at Kendall’s culinary skills in the caption of her video, writing, “Call The chef please cause the cookies were terrible.”
But she stopped there. For now.
“Guys, stop trying to get me to tell you more,” she said in a followup TikTok video shared Oct. 19. “I don’t gossip. I tell stories. There’s a big difference.”
She added, “I have plenty of stories just chill out…..”
Look back at Kendall’s dating history…
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“Anyways,” she continued, “it was just hilarious.”
The shade didn’t end there as Liv captioned the video, “Call The chef please cause the cookies were terrible.”
E! News has reached out to Kendall’s rep for comment and has not heard back.
But as for whether she plans to share insight into her older brother’s two-year on-again, off-again relationship with Kendall, which ended in 2020, that remains to be seen.
“Guys, stop trying to get me to tell you more,” she teased in a follow-up TikTok video shared Oct. 19. “I don’t gossip. I tell stories. There’s a big difference.”
DARA / BACKGRID; TikTok
She added, “I have plenty of stories just chill out…..”
Kendall and Ben, who sparked dating rumors in 2018, had largely kept their relationship private. However, in 2019, the reality star shared insight into her mindset navigating dating while living under public scrutiny.
“For me, a lot of things are very special and very sacred, like my friends and relationships, and I personally think that bringing things into the public makes everything so much messier,” she told Vogue Australia. “Also I’m very young and right now I feel like relationships aren’t always super-certain.”
In fact, Kendall didn’t “want to bring too much attention to something” without knowing what it will look like in the long term.
“A relationship is only meant to be between two people,” she added, “and the second you make it the world’s business is when it starts messing with the two people mentally. Like once everyone is let in, you’re letting all these opinions into your relationships, and I don’t think that’s fair.”
And Kendall has continued to block out the outside noise as she’s dated in the public eye. For a look back at her high-profile romances, keep reading.
Harry Styles
“No story, we’re friends,” Kendall Jenner told E!’s Giuliana Rancic in November 2013 of her and Harry Styles‘ relationship status after they were spotted at dinner in West Hollywood. “He’s cool.”
But subsequent sightings in New York and London even had Brody Jenner guessing that, whatever was up between them, his half-sister was in the driver’s seat.
“I’m sure she’s having a fun time with him,” he told the New York Daily News that December. “She has a very level head, great head on her shoulders. But they are both so young.”
Then 18 and 20, Kendall and Harry never lost each other’s numbers, reuniting for stop-the-presses outings in 2016 (including a PDA-packed stay aboard a yacht), 2018, 2020…
So, at the very least, a lasting friendship was in the cards for the duo, who sparked romance rumors again as recently as 2022following Harry’s split from Olivia Wilde.
“She and Harry are just good friends,” a source told E! News at the time. “They remained friendly over the years and have kept in touch.”
Justin Bieber
Nick Jonas
In August 2015, freshly single Nick Jonas was rumored to be seeing Kendall after being introduced into her orbit by brother Joe Jonas and his then-girlfriend Gigi Hadid.
But they weren’t on the level of dating, according to Nick.
“Kendall is great,” he told E! News at the time, “and naturally with her being good friends with Gigi and with Joe and Gigi dating, there are times we’ll be in the same place and we all hang out.”
Jordan Clarkson
A$AP Rocky
Blake Griffin
Ben Simmons
Ben Simmons actually courted Kendallthe pair meeting in the spring of 2018 and making an effort at meeting up whenever possible despite the point guard being based in Philadelphia. (Ironically, now he’s a Clipper, as of 2025.)
Kendall streamed a 76ers game during a photo shoot with Australian Vogue in the spring of 2019, according to the subsequent cover story, and then FaceTimed the Melbourne native to show off her copy of his recent GQ Australia cover.
“For me, a lot of things are very special and very sacred, like my friends and relationships, and I personally think that bringing things into the public makes everything so much messier,” the model told Australian Vogue. “Also I’m very young and right now I feel like relationships aren’t always super-certain.”
By the first Monday in May—i.e. the Met Gala—in 2019, they had amicably split upKendall foreseeing that her packed schedule could pose too many complications.
As she told Australian Vogue“Everyone has their own path and their own way of letting the cards fall. Your 20s are for messing up and figuring it out.”
Meanwhile, the Internet had sensed a pattern. A fan tweeted a meme in 2019, “Starting 5 of NBA Players Kendall Jenner Dated,” that boasted photos of Jordan, Ben, Blake, then-Laker Kyle Kuzma and journeyman 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.”
Devin Booker
Kendall dated Devin Booker for almost two years starting in 2020even bringing the Phoenix Suns shooting guard as her date to sister Kourtney Kardashian‘s Italian nuptials in May 2022.
But by the following month they were taking time apart, a source telling E! News that, after they got back from their trip, “they started to feel like they weren’t aligned and realized they have very different lifestyles.”
It was game on again that July, but by November they were going their separate waystheir schedules still not compatible. (Though he bumped D’Angelo out of “Kendall’s Starting Five” by the time Kim Kardashian got her hands on a T-shirt version of the meme.)
More recently, a Valentine’s Day weekend sighting of the snow-goggles-sporting pair sitting side-by-side at an Aspen restaurant in 2025 showed that one’s 20s really are for letting things happen and figuring it out.
Bad Bunny
Bad Bunny hopped into Kendall’s life in 2023, and they were first spotted in February on an apparent double date with Justin and Hailey Bieber.
Then Kendall caught the Puerto Rican artist’s set at Coachella in April, and the following month they slipped into a Met Gala afterparty together and twinned at a Lakers game.
Numerous date nights ensued, and they sat together at the Gucci show during Milan Fashion Week that September, but they were no longer a couple by the end of the year.
However, because if you can stay friends then why not, the duo, who have mutual pals, have reunited numerous times since, all over the world.
And not one to resist a runway-side seat, Bad Bunny was in the audience to see Kendall walk the walk for Calvin Klein Collection’s Autumn/Winter 2025 show during New York Fashion Week in February.
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