Sydney Sweeney goes undercover as Scooter Braun takes her to Times Square for first time

The pair was all smiles as they were seen enjoying on a fun date
Sydney Sweeney and Scooter Braun were seen at the Times Square (Instagram/@scooterbraun)
Sydney Sweeney and Scooter Braun were seen at the Times Square (Instagram/@scooterbraun)

NEW YORK CITY, NEW YORK: Sydney Sweeney and Scooter Braun spent their night at Times Square on Saturday, May 30, in a very unconventional yet fun way as the two went undercover to enjoy themselves among the crowd.

Braun documented their outing in a video which he also posted on Instagram and wrote, 

When you’re in bed at 11pm and your girl says ‘I’ve never been to Times Square….’😂.”

Sydney Sweeney dances to Jay-Z’s ‘Empire State of Mind’ 

It shows the pair in hoodies as they ride bikes and eat burgers. The 44-year-old businessman’s social media reel also shows the ‘Euphoria’ star excitedly posing in front of her recent American Eagle ad and on the very famous ruby red steps.

Sweeney can even be seen dancing to Jay-Z’s ‘Empire State of Mind’ as people around her failed to recognize her.

Sydney Sweeney enjoys her time in Times Square (Instagram/ @scooterbraun)
Sydney Sweeney enjoys her time in Times Square (Instagram/@scooterbraun)

Sydney Sweeney wore little black dress for date night

Earlier in the evening, Sweeney and Braun even went on date as the actress, 28, looked sexy in a black dress with plunging neckline. She added a pair of Louboutin stilettos and a little black bag to complete her look.

The former talent manager looked equally smart as he donned an all-black outfit for the romantic outing.

Sydney Sweeney and Scooter Braun 'are the real deal'

Sweeney and Braun reportedly began dating after meeting at Lauren Sánchez and Jeff Bezo’s wedding in June 2025.

Sydney Sweeney (L) and Scooter Braun are seen on the Upper East Side on May 30, 2026 in New York City. (Photo by TheStewartofNY/GC Images)
Sydney Sweeney (L) and Scooter Braun are seen on the Upper East Side on May 30, 2026 in New York City (TheStewartofNY/GC Images)

Later, a source reportedly shared that the two “are still seeing each other and trying to be as low-key as possible, while still dating and having fun. They are just taking things slow and enjoying their time together.”

Another insider reportedly disclosed that the couple “are the real deal, and their relationship has become very serious.”

“Sweeney really appreciates Scooter’s support with all her projects. [She] loves hearing his feedback,” they added.

Regarding Braun, the source noted that he’s “emotionally invested in her career and wants the best for her.”

Scooter Braun calls Sydney Sweeney 'extraordinary woman'

Meanwhile, recently when Braun was asked about ‘The Housemaid’ star’s raunchy performance in ‘Euphoria’ in an interview, he replied, “I am biased, I like it. I think there’s been an incredible performance by a certain actress.”

Sydney Sweeney and Scooter Braun are seen on November 4, 2025 in New York City. (Photo by XNY/Star Max/GC Images)
Sydney Sweeney and Scooter Braun are seen on November 4, 2025 in New York City (XNY/Star Max/GC Images)

He also gushed about her without taking her name as he added, “I’ve met an extraordinary woman, kind and generous and smart, and real and down-to-earth.”

Also, a tipster has previously shared that “Scooter has absolutely no issue with Sydney’s more provocative scenes in Euphoria or any of the work she does as an actress. He fully understands that it’s part of her job and respects how dedicated she is to her craft.”

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