The Post-Split Life: 7 Shocking Updates On Harry Styles And Olivia Wilde’s Careers And Current Dating Status In 2025

The whirlwind romance that captivated the world—and arguably overshadowed the film they made together—came to a quiet end in late 2022, but the story of Harry Styles and Olivia Wilde is far from over. As of late 2024 and early 2025, both stars have navigated significant career shifts and new, high-profile relationships, moving decisively into a new chapter of their lives. The intensity of their two-year relationship, which began on the set of the highly controversial film Don't Worry Darling, has given way to separate paths, yet the public fascination with their individual trajectories remains at an all-time high.

The split was initially framed as a "break" due to the pressures of Harry’s demanding global tour schedule and Olivia's focus on her children and directorial career. However, the true aftermath reveals a story of scrapped albums, a controversial new beau for Wilde, and the lingering shadow of Hollywood's most talked-about on-set drama. The following is a deep dive into the seven most significant updates and revelations about the lives of Harry and Olivia since they parted ways.

Comprehensive Biographies: The Director and The Global Superstar

To fully appreciate the scope of their separate lives, a look back at their monumental careers is essential. They are two of the most powerful entities in their respective industries, which only amplified the media scrutiny of their relationship.

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Harry Styles: The Pop Icon and Actor

• Full Name: Harry Edward Styles
• Born: February 1, 1994 (Age 31 in 2025)
• Birthplace: Redditch, Worcestershire, England
• Career Milestones:
  • Rose to global fame as a member of the boy band One Direction (2010–2016).
  • Launched a critically acclaimed solo career with his self-titled debut album (2017), followed by the Grammy-winning Fine Line (2019) and Harry's House (2022).
  • Made his acting debut in Christopher Nolan’s war film Dunkirk (2017).
  • Starred as Jack Chambers in the psychological thriller Don't Worry Darling (2022).
  • Known for his flamboyant, boundary-pushing fashion and gender-fluid style.

Olivia Wilde: The Acclaimed Actress and Director

• Full Name: Olivia Jane Cockburn
• Born: March 10, 1984 (Age 41 in 2025)
• Birthplace: New York City, New York, USA
• Career Milestones:
  • Gained recognition for her role as Alex Kelly on the teen drama The O.C. (2004–2005).
  • Achieved widespread fame as Dr. Remy "Thirteen" Hadley on the medical drama House (2007–2012).
  • Starred in major films including TRON: Legacy (2010) and Her (2013).
  • Made her critically acclaimed directorial debut with the comedy Booksmart (2019).
  • Directed and starred in Don't Worry Darling (2022), where she met Harry Styles.
  • Was previously engaged to actor Jason Sudeikis, with whom she shares two children, Otis and Daisy.

1. Harry Styles Scrapped a "Heartbreak Album" After the Split

One of the most surprising and fresh revelations in the aftermath of the breakup is the existence of a body of work that may never see the light of day. According to sources close to the pop star, Harry Styles reportedly recorded an entire album focused on the heartbreak and emotional turmoil following his split from Olivia Wilde.

This "heartbreak album" was said to be a collection of deeply personal and sad songs, but the material was ultimately scrapped. Styles, known for his upbeat and universally joyful pop hits like "As It Was," may have decided to shelve the project to maintain his artistic trajectory or to keep the emotional fallout from the relationship private. This decision leaves fans wondering what raw, emotional depth was contained in those unreleased tracks, a stark contrast to his public image.

2. Olivia Wilde's New High-Profile Romance with Dane DiLiegro

While Harry Styles has kept a low profile on the dating front since mid-2024, Olivia Wilde has moved on with a new, equally high-profile partner: actor and former professional basketball player Dane DiLiegro. The relationship has been a major talking point in early 2025, confirming that Wilde has fully closed the chapter on her romance with Styles.

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DiLiegro, a towering 6'9" former athlete who played basketball in Italy, is now known for his acting roles, often playing creature characters, such as the Predator in Prey. The couple was spotted together at a Lakers vs. Celtics game in January 2025, marking one of their most public appearances and solidifying their status as an item. Sources indicate that the two share a lot in common and are enjoying their time together, signaling a significant new phase in Wilde's personal life.

3. Harry Styles is Reportedly Single After Taylor Russell Split

Following his split from Wilde, Harry Styles entered into a relationship with Canadian actress Taylor Russell, known for her roles in Bones and All and Lost in Space. The pair first sparked dating rumors in June 2023 and were spotted together numerous times, maintaining a relatively private relationship compared to his time with Wilde.

However, reports from May 2024 confirmed that Styles and Russell had broken up after less than a year of dating. Sources suggested the split came after a "rough patch" following a trip to Japan, with the couple deciding to take time apart. As of early 2025, Harry Styles is widely believed to be single, focusing on his creative projects and preparing for his next major career move, which has fueled intense speculation about his upcoming fourth studio album.

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4. The Enduring Legacy of the 'Don't Worry Darling' Controversy

The relationship between Styles and Wilde will forever be intertwined with the behind-the-scenes drama of their film, Don't Worry Darling. While the film was a commercial success, its release was overshadowed by a series of high-profile controversies that continue to define its legacy.

• The Florence Pugh Feud: Rumors of tension between director Olivia Wilde and lead actress Florence Pugh dominated the press, with Pugh notably limiting her promotional duties for the film.
• Shia LaBeouf's Casting: The public dispute over whether Wilde fired LaBeouf or if he quit the film added another layer of complexity.
• "Spitgate": The bizarre, viral moment at the Venice Film Festival where many speculated Harry Styles spat on co-star Chris Pine's lap. Pine's representatives vehemently denied the rumor, but the incident became a definitive meme of the film's chaotic press tour.

Wilde has since reflected on the media frenzy, often attributing the intense scrutiny to the double standards faced by women directors in Hollywood. Despite the controversy, the film remains a key entity in the careers of both stars, a constant reminder of the intense pressure cooker that sparked and ultimately ended their romance.

5. Harry Styles’ Anticipated Fourth Album and 2026 Tour

With the Love On Tour finally concluded, the focus for Styles has shifted entirely to his next musical project. The anticipation for his fourth studio album (often referred to by fans as 'HS4') is immense. While the heartbreak album was reportedly scrapped, new reports suggest that Styles has completed the work on his next album and is planning a massive 2026 world tour.

The new music is expected to build on the success of Harry's House, potentially exploring new sounds while maintaining his poetic and romantic lyricism. The lead single, rumored to be titled "Like Magic," is speculated to drop in 2025, marking his official return to the public eye after a period of relative quiet following his breakup and subsequent short-lived relationship.

6. Olivia Wilde’s Focus on Directorial Projects

Since the release of Don't Worry Darling, Olivia Wilde has doubled down on her career behind the camera. Her critical success with Booksmart established her as a formidable director, and her next projects are highly anticipated. She has been actively developing several new films, including a potential biopic and a female-driven project, prioritizing her role as a filmmaker over her acting career in 2025. This focus on directing allows her to maintain creative control and distance herself from the celebrity gossip that dominated the DWD era.

7. The Co-Parenting Dynamic with Jason Sudeikis

A significant factor in Olivia Wilde's life remains her co-parenting relationship with her former fiancé, Jason Sudeikis. The timeline of her relationship with Harry Styles overlapped with the end of her nine-year engagement to Sudeikis, which was a source of much tabloid speculation. The former couple shares two children, Otis and Daisy, and the need to maintain a stable, functional co-parenting environment in Los Angeles was often cited as a reason for the geographical and logistical challenges in her relationship with the globe-trotting Styles. The current stability of their co-parenting arrangement is a priority for Wilde as she embarks on her new relationship with Dane DiLiegro.