Scooter Braun and Sydney Sweeney Go Undercover in Times Square

When your girlfriend mentions she’s never experienced something iconic, sometimes you hop out of bed at 11pm and make it happen. That’s exactly what music manager Scooter Braun did for actress Sydney Sweeney recently, whisking her off to New York City’s Times Square for a spontaneous adventure—disguises and all.

The couple pedaled through the Big Apple streets incognito, with Sweeney sporting a blue hoodie and black sunglasses while Braun opted for a gray hoodie and green baseball cap. They grabbed a burger, biked around, and Sweeney even serenaded the moment with Alicia Keys’“Empire State of Mind”while standing beneath an American Eagle billboard that happened to feature her own campaign. It’s the kind of romantic gesture that feels equal parts planned and purely in-the-moment—and their Instagram caption suggests Braun was still riding the high of the spontaneity when he posted the video on Sunday, May 31.

This latest outing marks another milestone in what insiders are calling a“very serious”relationship between the 44-year-old and the 28-year-old Euphoria actress. Braun and Sweeney were first romantically linked in summer 2025 after they were spotted together in Italy at Jeff Bezos and Lauren Sánchez’s star-studded wedding, but what started as a surprising pairing has clearly evolved into something deeper. By April, a source told Us Weekly that the couple are“blending their lives”in concrete ways—Braun has introduced Sweeney to his three children, Jagger, Levi, and Hart, while Sweeney has had Braun meet her brother, Trent, who apparently approves.

What’s striking about their relationship, according to insiders, is how emotionally invested both parties are in each other’s careers. Sweeney“really appreciates Scooter’s support with all her projects”and values his feedback, while Braun is“emotionally invested in her career and wants the best for her.”That kind of professional and personal alignment often signals staying power—especially when people around them had initially dismissed it as a fling. The fact that they’re moving past the honeymoon phase gossip and integrating families suggests they’re thinking longer-term. And clearly, Braun still knows how to keep the spark alive with midnight adventures to Times Square.