Ben Simmons’ Sister Trolls Kendall Jenner – Calls Her “Weird” & Roasts Her Baking Skills 🍪🔥
On October 20th, Olivia Simmons posted a Tik Tok in which she recounted a story about spending time with her brother and the Car Jenner sisters. Olivia, Ben Simmons sister, reminisced about her brother’s relationship with Kendall Jenner, recounting a cookie baking mishap. Simmons recounted a story in a Tik Tok posted on Saturday, October 20th, about a time when she, her brother, and the car Jenner sisters were playing cards against humanity and Kendall opted to make cookies for the event. Olivia, puzzled about her desire to bake, pointed out the viral clip of the reality star cutting cucumbers in a questionable manner during a May 2022 episode of the Kardashians. Olivia said she was like, “I am going to bake some cookies.” Since it was pre-prepared cookie dough, there wasn’t much to do other than ensure it was in the correct location at the correct time. The only thing you have to do is to cut them into pieces of equal size. Olivia stated this before stopping for a moment and then noticing how irregular the cookie slices were at that point. I have never seen so many uneven cookies. What is tarnation? She laughed. If you don’t, just call your chef to come and cook these cookies for you. In any case, it was all just so funny. In almost disbelief at what she had witnessed during that time, the sister went on to label the family a weird bunch. Dating speculation arose between the Australia born NBA player and Jenner in 2018 and Caitlyn Jenner later confirmed the relationship on the now canceled Ellen Degenerous show. So obviously you’re dating this guy who’s on the 76ers for a bit now. Caitlyn replied when host Ellen DeGeneres asked how long have you been dating him? The couple was seen in public occasionally but they opted to keep a very low profile concerning their relationship. Kendall discussed her reasoning for keeping their relationship as private as possible in an interview with Vogue Australia that year. She explained, “A relationship should only involve two people. The moment you turn it into something the world is involved in, that’s when it begins to affect those two people mentally. Once everyone is allowed in, you’re allowing all these opinions into your relationships, which I don’t think is fair.” In spring 2019, a close source to Kendall confirmed to People that the two were no longer exclusive and were actively on a break. The source disclosed, “The relationship ran its course. She is hanging out with her friends and has returned to fun mode.
Ben Simmons’ Sister Trolls Kendall Jenner – Calls Her “Weird” & Roasts Her Baking Skills 🍪🔥
we uncover the wild story of Ben Simmons’ sister trolling his ex-girlfriend, Kendall Jenner — and the internet can’t stop talking about it. From shady tweets to hilarious baking jokes, Olivia Simmons didn’t hold back as she mocked Kendall’s cooking skills and called her “weird.” This video explores every detail of their past relationship, what led to the breakup, and how this online drama reignited years later. We’ll also look at how fans reacted, what Kendall’s response might mean, and why this feud has everyone laughing and shocked at the same time.
Watch as we break down Ben Simmons’ history with Kendall Jenner, their high-profile romance, and the aftermath that continues to make headlines in 2025. From NBA courts to Hollywood kitchens — this story has it all: love, fame, shade, and a touch of humor that only the Kardashian-Jenner world can deliver.
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