Scooter Braun posted a May 31 Instagram video showing a rare, low-key late-night Times Square outing with Sydney Sweeney—while the Euphoria star’s personal and brand spotlight continues to intensify.
For a couple that has spent months being watched, the moment in Scooter Braun’s new video looks oddly quiet.
On May 31, Braun, 44, posted to Instagram a late-night clip from New York City’s Times Square with Sydney Sweeney, 28. The two rode electric bikes through the city. stopped for hamburgers. and then made their way to Seventh Avenue and 46th Street to look up at a digital billboard featuring Sweeney’s latest American Eagle campaign.
Braun set the scene in his caption: “When you’re in bed at 11pm and your girl says ‘I’ve never been to Times Square…’ ” In the video. Sweeney appears incognito in sunglasses. a blue oversized hoodie. and light-wash jeans. On the sidewalk. she briefly sang along to “Empire State of Mind. ” while passersby walked by without drawing attention to the pair. In one clip, Sweeney excitedly gave Braun a thumbs-up.
The outing lands in the middle of a growing public presence for their relationship. Nearly a year earlier. speculation sparked as Sweeney and Braun courted attention while in Italy for Jeff Bezos and Lauren Sánchez Bezos’ wedding. In recent weeks, they’ve been more open about being together. On May 1. Sweeney shared multiple photos of herself and Braun getting cozy at the Stagecoach Music Festival in Southern California. with Braun carrying the “The Housemaid” actress in bridal style and also lifting her onto his shoulders during a set.
That visibility comes as Sweeney’s career and public image keep colliding with spotlight and scrutiny. After courting controversy, she is now back in another American Eagle jeans advertisement, a campaign presence emphasized by the billboard the two stopped to admire during their midnight ride.
The tension in Braun’s video isn’t what people see—it’s what they don’t. In the same city where Sweeney’s face is playing to crowds through a digital ad, she and Braun appear to blend into ordinary night life, even as their relationship continues to be tracked.
Behind the scenes, Braun’s own history remains part of the public record. He is a high-profile talent manager who has worked with clients including Justin Bieber and Ariana Grande and once controversially owned the lion’s share of Taylor Swift’s catalog. Braun was previously married to Canadian cancer activist Yael Cohen, and they share three children. He filed for divorce in 2021, which was finalized in 2022.
Sweeney’s recent relationship status has also been a key detail in the story around her public life. She and her fiancé, Jonathan Davino, ended their engagement after nearly seven years together in early 2025.
Scooter Braun Sydney Sweeney Times Square American Eagle Instagram video electric bikes late-night outing Stagecoach Music Festival Jeff Bezos wedding Lauren Sánchez Bezos Jonathan Davino Yael Cohen Justin Bieber Ariana Grande Taylor Swift catalog