Ellen cheekily asks Harry Styles about his ex Kendall Jenner and things get very awkward: "When you..."

Harry Styles wasn't ready to be grilled by Ellen DeGeneres on her talk show, and it shows
(L-R) Screenshot of Harry Styles and Ellen DeGeneres from 'The Ellen Show'; (Inset) Kendall Jenner attends The 2024 Met Gala (Cover Image Source: YouTube | The Ellen Show; (inset) Getty Images | Photo by Cindy Ord)
(L-R) Screenshot of Harry Styles and Ellen DeGeneres from 'The Ellen Show'; (Inset) Kendall Jenner attends The 2024 Met Gala (Cover Image Source: YouTube | The Ellen Show; (inset) Getty Images | Photo by Cindy Ord)

Harry Styles made his final appearance on 'The Ellen Show' on December 18, 2019, which was a Christmas special and, as we all know, Ellen has a knack for making her guests super uncomfortable with some bizarre or personal questions. As for Styles, she certainly didn’t make things easy. During their conversation, she didn’t shy away from direct questions, like whether 'Fine Line' was inspired by a breakup (a not-so-subtle nod to his split with Camille Rowe, though she didn’t name names). And when the conversation turned to his other famous ex, Kendall Jenner, things got a little... well, awkward.



 

Styles, looking effortlessly stylish in a Stay Away from Toxic People sweater and a pearl necklace, was happily discussing his experience guest-hosting 'The Late Late Show for James Corden'. Then came DeGeneres’s question: "So when you hosted for James Corden, your guests were Tracee Ellis Ross and Kendall Jenner. And you and Kendall are really good friends now, right?" Styles responded, "Yeah, we’ve been friends for um, a while now, yeah. Like several years." DeGeneres slyly added, "That’s sweet that y’all are really good friends." Styles simply answered, "Yeah," Cosmopolitan reported.



 

Then came the true awkward moment. DeGeneres said, "Yeah," as she seemed ready to move on, but Styles threw in one last nervous remark—setting up a hilariously uncomfortable back-and-forth. "Yeah," he said again, sheepishly laughing. "I think so, yeah." Cue the ultimate awkward pause. DeGeneres matched his energy, with, "Yeah." Styles continued hesitantly, "Right." to which she also replied, "Right," which led to another awkward silent moment. The whole moment was not only awkward for both of them but also for the audience who had no idea what was about to happen next. Styles took a sip of his drink, finally breaking the weird tension with an "Okay." And then DeGeneres shifted gears, asking whether his album was about a breakup, another question Styles slyly dodged.



 

As for Styles, he has had his fair share of awkward interview moments over the years. On 'The Late Late Show with James Corden', Harry faced a solid awkward moment when Kendall's name came up, again in a conversation. Actor Aaron Taylor-Johnson, who was also a guest shared that his chickens were named after the Kardashians, including "Kendall." There was a noticeable pause, and  Styles looked around nervously before staring into his drink. The crowd clapped but he remained visibly uneasy. When Corden asked Styles, "Do they lay every day, Harry?" Styles literally turned away from the camera, adding more awkward tension to the moment.

Harry Styles performs on stage during The BRIT Awards 2023 at The O2 Arena on February 11, 2023 in London, England. (Credit Image Source: Getty Images | Photo by Gareth Cattermole)
Harry Styles performs on stage during The BRIT Awards 2023 at The O2 Arena on February 11, 2023 in London, England. (Credit Image Source: Getty Images | Photo by Gareth Cattermole)

Though Styles hasn't dropped names, he hinted in a Rolling Stone interview that one woman inspired much of the album. He said, "She's a huge part of the album… Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap… and hope they know it's just for them." Styles' fans are well aware of his past relationships, so these interviews are sure to bring up his exes—and we can definitely expect a few awkward moments.

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