When she wasn’t slinging undies into the crowd at Stagecoach festival, all eyes were on Sydney Sweeney and the initials hanging off her neck.
Eagle-eyed fans spotted the Euphoria star, 28, wearing a dainty necklace with an ‘SB’ charm, seemingly a nod to her long-rumoured boyfriend Scooter Braun, 44.
Days later, she finally hard-launched her relationship with the controversial music executive, sharing a series of loved-up photos from the event to Instagram.
But this isn’t the first time her love life has made headlines.
From her engagement to businessman Jonathan Davino, 42, to her rumoured romance with co-star Glen Powell, 37, and now her relationship with the mega music executive – here’s how Sweeney’s love life became one of the most talked about this year.
A tangled timeline
Sweeney and Braun, who is known for his famous feud with Taylor Swift, appeared to confirm their relationship with a single photo in October 2025.
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The two stepped out in New York City together after rumours of a romance kicked off in June, and most recently were seen dancing together at the April 2026 Stagecoach festival.
In a carousel of photos Sweeney shared from the event, marking Braun’s debut on her Instagram grid.
The pair looked rather cosy, with photos showing the actress on Braun’s shoulders in the crowd and being held in his arms, and several photobooth pics of the pair.
“cowboy kind of weekend,” the caption read.
Before Braun, Sweeney was engaged to businessman Jonathan Davino. The pair were in a long-term relationship from 2018 until their engagement ended in March 2025.
Early that year, the rom-com actress was asked by The Times if she was still wedding planning, and simply replied, “No,” before confirming she was single.
“I’m learning a lot about myself, spending more time with my friends. And I’m loving it.”
But here’s where things get complicated.
Glen Powell comes along
In December 2023, Sweeney starred alongside Glen Powell in the romantic comedy Anyone But You, filmed in Sydney.
While romance rumours have now been debunked, fans – and the press – couldn’t help but notice their on-screen chemistry, despite the actors having their own respective relationships at the time.
Sweeney was with Davino and Powell with Gigi Paris; both relationships had since ended, adding to speculation of a romance between the co-stars.
The rumours dragged on for a year.
Powell’s mum, however, cleared things up to The Daily Mail, in April 2025 saying: “They’re definitely not together.”
She said Sweeney is actually good friends with Powell’s sister Leslie and even attended her wedding.
Sweeney confirms her split from Davino
The actress confirmed her split from her former fiancé in an interview with The Times published on 31 May 2025.
“I’m learning a lot about myself, spending more time with my friends. And I’m loving it,” Sweeney told the publication.
Weeks later in June 2025, Sweeney attended Jeff Bezos and Lauren Sanchez’s lavish Venice wedding. Braun was also there.
Soon after the Bezos wedding, TikTok clips began to surface of the pair strolling through the Italian city together.
By September 2025 multiple publications, including People and TMZ, reported they were casually dating.
That brings us back to October 2025 when a single photo appeared to confirm the relationship.
Raising eyebrows
The relationship has raised eyebrows because Braun is known to be a controversial figure in the music industry.
The producer, who has worked with the likes of Justin Bieber, Kanye West, Usher and Ariana Grande, first waded into hot water when he purchased the record company Big Machine Label Group, which owned the rights to the majority of Taylor Swift’s back catalogue.
He later sold Swift’s catalogue to Shamrock Capital, despite allegedly knowing she wanted to acquire it – a move that prompted the singer to begin re-recording her old songs before finally reclaiming her original masters in 2025.
Braun has also reportedly cut ties with several musicians over the years, including Bieber and Grande.
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