Harry Styles and Olivia Wilde: A Complete Relationship Timeline | Glamour

The Whirlwind Romance Of Olivia Wilde And Harry Styles: A Full Timeline

Harry Styles and Olivia Wilde: A Complete Relationship Timeline | Glamour

By  Winona McKenzie

Table of Contents:

Introduction: The Unforgettable Duo

The entertainment world is no stranger to unexpected romances, but few captured the global imagination quite like the relationship between director Olivia Wilde and music sensation Harry Styles. Their journey, which began on the set of a highly anticipated film, unfolded under an intense spotlight, sparking countless headlines, fan theories, and public discussions. This article delves deep into the captivating story of Olivia Wilde and Harry Styles, from their initial meeting to their eventual separation, providing a comprehensive timeline and exploring the key moments that defined their two-year romance.

From the moment whispers of their connection first emerged, the internet was sent into a frenzy. Fans and media alike eagerly followed every development, from subtle social media interactions to very public appearances. Their relationship was a focal point of discussion, especially given the circumstances surrounding its beginning and the high-profile nature of both individuals. Join us as we unpack the details of this intriguing chapter in celebrity romance, seeing the photos and details of their romance from September 2020 to May 2024, as reported by various media outlets, even though their relationship officially concluded earlier.

Olivia Wilde: A Brief Biography

Olivia Wilde, born Olivia Jane Cockburn, is an accomplished American actress and filmmaker. Hailing from a family with deep roots in journalism and media—her father, Andrew Cockburn, is a journalist, and her mother, Leslie Cockburn, is a journalist and producer—Wilde has carved out a significant career in Hollywood. She transitioned from a successful acting career, with notable roles in television series like "House" and films such as "Tron: Legacy" and "Rush," to becoming a respected director. Her directorial debut, "Booksmart" (2019), earned critical acclaim for its fresh take on the coming-of-age genre. Her work often touches upon themes of female empowerment and social commentary, earning her a distinct voice in the industry. Before her relationship with Harry Styles, Wilde was notably in a long-term partnership with actor Jason Sudeikis, with whom she shares two children, Otis and Daisy.

Personal Data: Olivia Wilde

AttributeDetail
Full NameOlivia Jane Cockburn
BornMarch 10, 1984
Age (at relationship start)~36 (late 2020)
NationalityAmerican
OccupationActress, Director, Producer, Activist
Notable Works (as director)Booksmart (2019), Don't Worry Darling (2022)
Notable Works (as actress)House (TV series), Tron: Legacy, Rush

Harry Styles: A Brief Biography

Harry Styles is a global phenomenon, first rising to superstardom as a member of the massively successful boy band One Direction. Formed on "The X Factor" in 2010, One Direction became one of the best-selling boy bands of all time, launching Styles into instant international fame. Following the band's hiatus in 2016, Styles embarked on an equally impressive solo career, establishing himself as a critically acclaimed musician with chart-topping albums like "Fine Line" (2019) and "Harry's House" (2022). His music, characterized by a blend of pop, rock, and folk influences, has earned him numerous awards, including multiple Grammy Awards. Beyond music, he has ventured into acting, appearing in Christopher Nolan's "Dunkirk" (2017) and later starring in "Don't Worry Darling." His distinctive fashion sense, often challenging traditional gender norms, has made him a style icon, frequently gracing magazine covers and influencing trends. His private life, though often guarded, has always been a subject of immense public interest, making his relationship with Olivia Wilde particularly noteworthy.

Personal Data: Harry Styles

AttributeDetail
Full NameHarry Edward Styles
BornFebruary 1, 1994
Age (at relationship start)~26 (late 2020)
NationalityBritish
OccupationSinger, Songwriter, Actor, Model
Notable Works (Music)Fine Line (2019), Harry's House (2022), "As It Was" (single)
Notable Works (Film)Dunkirk (2017), Don't Worry Darling (2022), My Policeman (2022)

How Olivia Wilde and Harry Styles First Met: The Don't Worry Darling Connection

The genesis of the relationship between Olivia Wilde and Harry Styles is intrinsically linked to the film "Don't Worry Darling." Olivia Wilde directed this 2022 American psychological thriller, a project that garnered significant attention even before its release. The screenplay, initially a spec script by Carey Van Dyke and Shane Van Dyke, was later refined by Katie Silberman, who also contributed to Wilde's vision for the film, focusing on a story that explores themes of control, conformity, and female pleasure. It was on the set of this highly anticipated movie that their paths truly converged, setting the stage for one of Hollywood's most talked-about romances.

Harry Styles joined the cast in late 2020, replacing Shia LaBeouf, who had initially been cast in the male lead role of Jack. This casting decision was a significant moment, not just for the film but, as it turned out, for Wilde's personal life. The opportunity to work with Styles, whose star power was immense, was clearly exciting for Wilde. Interviewed as part of Styles's Vogue cover story, Wilde openly discussed her reaction to casting the former One Direction star. She described a "victory dance" after securing him for the role, highlighting her profound enthusiasm for his talent, charisma, and presence on screen. This early interaction on set, where they spent countless hours collaborating creatively, laid the groundwork for what would become a highly publicized romance. Olivia Wilde and Harry Styles began dating in late 2020, shortly after Wilde's split from Jason Sudeikis, taking fans by surprise with their whirlwind romance that began when they met on the set of "Don’t Worry Darling." The chemistry, both on and off-screen, became palpable, quickly escalating beyond professional boundaries.

The Whirlwind Begins: From Set to Public Appearance

While their connection began subtly on the set of "Don't Worry Darling," it wasn't long before the relationship between Olivia Wilde and Harry Styles became a subject of intense speculation and public interest. The duo made headlines when they were first photographed together, signaling that their professional collaboration had blossomed into something more profound. The earliest concrete public confirmation came in January 2021, a mere few months after filming began. Harry Styles and Olivia Wilde were photographed holding hands at a wedding in Montecito, California, specifically that of Styles's manager, Jeffrey Azoff. This seemingly casual yet intimate gesture, captured by paparazzi, sent shockwaves through social media and entertainment news outlets, definitively confirming what many had already suspected and sparking immediate discussion about their relationship status.

This initial public appearance solidified their status as a couple, and from that point, their romance was under constant scrutiny. Despite the intense public interest, both Olivia Wilde and Harry Styles generally maintained a degree of privacy regarding their personal lives, a challenge given their immense fame. Styles, in particular, had previously expressed his desire to keep his personal life under wraps, telling Rolling Stone in August [of 2022] that he also wanted to keep his personal life under wraps, a sentiment he has often reiterated throughout his career. However, the sheer magnitude of their combined fame meant that every sighting, every subtle hint, was dissected by fans and media alike. Their relationship was going strong nearly a year after Page Six broke the news that they were dating, indicating a period of stability despite the constant attention and the challenges of navigating two demanding careers. Things seemed to be going in the right direction for the couple, even with the ever-present public eye.

Navigating the Public Eye: Red Carpets, Rumors, and Reactions

The relationship between Olivia Wilde and Harry Styles was perpetually under the microscope, especially with the impending release of "Don't Worry Darling." The film itself became intertwined with their personal lives, leading to heightened anticipation and, at times, controversy. The Venice International Film Festival in September 2022 was a prime example of this intense public scrutiny and the media circus that surrounded them. Olivia Wilde, Sydney Chandler, and Harry Styles attended the "Don't Worry Darling" red carpet at the 79th Venice International Film Festival on September 05, 2022. This event, in particular, sent the internet into a frenzy, especially

Harry Styles and Olivia Wilde: A Complete Relationship Timeline | Glamour
Harry Styles and Olivia Wilde: A Complete Relationship Timeline | Glamour

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Harry Styles and Olivia Wilde Share Kiss in London
Harry Styles and Olivia Wilde Share Kiss in London

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Every time Harry Styles and Olivia Wilde have twinned
Every time Harry Styles and Olivia Wilde have twinned

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