Scooter Braun and Sydney Sweeney were spotted enjoying a low-key night out in New York City, with Braun sharing a May 31 Instagram video that documented their undercover-style date. The clip showed the pair biking through the city while wearing casual disguises, with Sweeney in a blue hoodie and black sunglasses and Braun in a gray hoodie and green baseball cap. Braun captioned the post with a playful remark about being in bed at 11 p.m. before hearing that Sweeney had never been to Times Square.
The video followed the couple as they made their way through New York and stopped to eat. At one point, Sweeney was seen sitting at a high-top counter and eating a burger while Braun asked how it tasted. She replied that it was “really good” as she continued eating. The brief moment added to the relaxed, playful tone of the outing, which seemed designed to keep things private while still allowing them to explore the city together.
Their night ended in Times Square, where Sweeney stood under the bright lights and danced to Alicia Keys’ “Empire State of Mind.” She also posed in front of a digital billboard featuring her American Eagle campaign ad, turning the unexpected excursion into a memorable photo moment. The appearance highlighted both the iconic setting and Sweeney’s high-profile fashion and brand presence.
Braun’s post gave followers a glimpse of the pair’s chemistry and their casual approach to the evening. Rather than a formal red-carpet appearance or a heavily staged outing, the video showed them blending into the city, riding bikes, grabbing food, and taking in one of New York’s most famous landmarks. The tour also underscored Sweeney’s first visit to Times Square, making the experience feel new and spontaneous.
The social media post quickly drew attention because of the unexpected pairing and the intimate, off-duty nature of the content. Braun, 44, and Sweeney, 28, appeared relaxed and comfortable throughout the footage, with the lighthearted style of the video suggesting a fun late-night adventure rather than a public appearance. The combination of New York City sightseeing, street food, and a billboard cameo created a polished but informal snapshot of their night together.
By sharing the experience online, Braun turned a private-looking outing into a buzzy moment that mixed celebrity culture, romance, and a quintessential New York backdrop. The result was a video that presented the pair as playful, understated, and very much in step with the energy of the city they were exploring.
