Inside Glen Powell's dating timeline from Vampire Diaries star to Sydney Sweeney rumours

Glen Powell has emerged as one of Hollywood's most sought-after leading men, with admirers eager to discover everything about the Chad Powers star's romantic history.

Disney+ is launching sports comedy Chad Powers this week on Tuesday, September 30, featuring Glen Powell as former quarterback legend Russ Holliday who obliterates his career during a crucial match.

Eight years on and desperate to return to the pitch, he transforms himself into "Chad Powers" and joins a faltering football squad in his quest to reclaim his past success.

Admirers have previously adored watching the 36-year-old in romantic comedies such as Anyone But You alongside Sydney Sweeney and 2018's Set It Up featuring Zoey Deutch.

With Powell making his return to our screens in a completely different capacity, let's examine the star's romantic past to date.

Vampire Diaries legend Nina Dobrev marked Powell's first major public romance when dating speculation emerged in January 2017 following their New Year's celebration with friends in Texas.

He also attended her La La Land themed birthday celebration that month, where they costumed themselves as Emma Stone and Ryan Gosling's characters and replicated their iconic pose from the movie.

However, later that year, it emerged that the duo were taking a breather due to their hectic schedules.

Despite this, they appear to have maintained a friendly relationship as she was spotted at the London premiere of his film Top Gun: Maverick in 2022, alongside Olympic snowboarder Sean White, her former fiance.

Not long after his break up with Dobrev, the actor was linked to Australian television presenter Renee Bargh.

They were spotted together at his 1980s themed birthday bash in November 2018, which was also attended by Dobrev, Chord Overstreet, John Stamos and other celebrities.

Sadly, this romance was short-lived as a year later, she revealed to the Daily Mail that she was single and on the hunt for a "good Aussie boy".

Powell was first associated with model Gigi Paris five years ago when they were seen enjoying a romantic getaway in Mexico, but they didn't make their relationship Instagram official until a year later.

They were an item for three years, but their split was confirmed in April 2023 when a source told People: "Gigi and Glen had broken up several times.

"They had been on shaky ground since Top Gun was released. Gigi was never content with the long-distance filming, and when she visited Australia [where Powell was shooting Anyone But You] they both decided to call it quits for good."

Despite both Powell and Sweeney denying any romantic involvement, fans have been speculating due to their undeniable on-screen chemistry in Anyone But You.

Sweeney was engaged to producer Jonathan Davino during filming but ended their relationship in May 2025.

Powell previously told Business Insider that their flirtatious banter increased while promoting the film.

He confessed: "I'll pretty much give Sydney all the credit for this.

"I don't have the mental capacity to pull anything like this off, but she's very smart. She's very smart.

"I had such a wonderful journey with her on this thing."

Chad Powers premieres on Tuesday, September 30, on Disney+.