Rumors Are Swirling Harry Styles Is Hanging Out With Kendall Jenner Following Split From Olivia Wilde

Harry Styles’ love life was a massive topic of conversation for a while now, as the One Direction alum was in a relationship with his Don’t Worry Darling director, Olivia Wilde. The pair garnered quite a bit of attention amid their romance, and it tangentially became connected to the drama surrounding Wilde’s latest movie. Earlier this month, it was reported that the two are “taking a break” from their nearly two-year relationship. Interestingly enough, new rumors now claim that in the aftermath of the breakup, Styles is hanging out with an old flame – Kendall Jenner. 

Harry Styles and Kendall Jenner, who dated off and on between 2013 and 2019, have allegedly been spending time together as of late. According to one of The Sun, Jenner has served as a source of support for the singer in the wake of his split from Olivia Wilde. The two may not have been able to make things work romantically, but it sounds like they still share a close bond due to their unique statuses: 

Harry and Kendall have always stayed in touch, but in light of their recent splits, they have more time for one another. 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.

Alleged friends of the stars also noted that the timing of these purported meet-ups is “interesting,” considering what the model and reality TV alum is going through at the moment. The Kardashians alum and Phoenix Suns phenom Devin Booker recently broke up after dating for over two years. With that information in mind, it’s hard not to look at this information from a suspicious point of view. However, the source also says that these recent engagements may not necessarily indicate romantic sparks:

Close as they are, Harry and Kendall found dating difficult, and all of those practical problems they faced years ago are still there. 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.

You have to wonder if Harry Styles would really be willing to jump into a new relationship after his time with Olivia Wilde. In January 2021, he was first linked to Wilde, who’d split from longtime partner Jason Sudeikis months prior. There’s been much speculation regarding whether Wilde and Styles’ romance overlapped with her previous one. Wilde and Sudeikis’ former nanny claimed that was the case. However, the Booksmart director shut down rumors that she left Sudeikis for Styles. On top of all this, there was also the alleged feud between Wilde and Florence Pugh, the leading lady of Don’t Worry Darling. In October, it was said that the couple’s relationship was withstanding the drama, though. 

Recent events would suggest that Harry Styles and Olivia Wilde are indeed done, though the jury is definitely still out on him and Kendall Jenner. It’ll be interesting to see whether the two actually do end up rekindling their love or if (or when) the singer ends up with another person entirely. 

Those who are already nostalgic for the “WildeStyles” can see the two acting alongside each other in Don’t Worry Darling, which is available to stream using an HBO Max subscription.

Erik Swann
Senior Content Producer

Covering superheroes, sci-fi, comedy, and almost anything else in film and TV. I eat more pizza than the Teenage Mutant Ninja Turtles.