Styles is reportedly on a break from his relationship with Olivia Wilde, whom he had been dating for the past two years since being cast in her psychological thriller Don't Worry Darling. Meanwhile, multiple outlets recently reported that Jenner and her NBA star boyfriend of two years, Devin Booker, have broken up for a second time.
Now, it seems that Styles and Jenner, who have been romantically linked on multiple occasions starting in 2013, may have rekindled their connection amid their breakups.
"Harry and Kendall have always stayed in touch, but in light of their recent splits, they have more time for one another," an insider told The Sun. "And Harry has had Kendall's ear over his break-up with Olivia. Kendall is one of the few people to understand the level of fame and scrutiny which Harry endures. She is also dealing with her own tough time."
The Sun also noted that the two have been "leaning on each other" in the past few weeks.
The former flames have maintained a friendship long after their romance ended. Back in 2019, Jenner even made a guest appearance on The Late Late Show when Styles filled in for host James Corden.
Fans have been speculating about the former couple since Jenner attended one of Styles's Los Angeles concerts earlier this month. Video footage captured the model dancing alongside friend Hailey Bieber and sister Kylie Jenner, and one viral TikTok even alleged that the singer blew a kiss to Jenner during his song "Love of My Life" (which many believe is about her).
Still, The Sun's source added that their renewed post-breakup connection may just be platonic.
"Close as they are, Harry and Kendall found dating difficult, and all of those practical problems they faced years ago are still there," the source continued. "That said, their friends speculate that they might hang out over the holidays. In the past they have gone away together shortly after respective break-ups, so they could very well end up on a yacht soaking up the sun in the next couple of months."
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