Sydney Sweeney and Scooter Braun tried to keep a late-night New York City outing low-key, but Times Square made that almost impossible.
Braun shared an Instagram video on May 31 showing himself and Sweeney biking through Manhattan in hoodies and sunglasses before ending the night in one of the brightest places in the city. E! News reported that Braun captioned the video, “When you’re in bed at 11pm and your girl says ‘I’ve never been to Times Square….’”
The clip gave the outing a simple hook: Sweeney wanted to see Times Square, Braun filmed the late-night trip, and the pair tried to blend in while visiting one of the least subtle places in New York.
Their Low-Key Night Included Bikes, Burgers and Hoodies
Braun, 44, and Sweeney, 28, wore casual disguises for the outing. E! reported that Sweeney wore a blue hoodie and black sunglasses, while Braun wore a gray hoodie with a green baseball cap underneath.
The video showed them riding through New York before stopping for food. Sweeney was later seen eating a burger as Braun asked how it tasted. She replied, “It’s really good.”
The Times Square visit was not a red-carpet appearance or a formal couple statement. It looked more like a spontaneous tourist run, which is probably why the clip traveled so quickly.
Sweeney Ended Up Under Her Own Billboard
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The most public part of the night came after the pair reached Times Square.
Sweeney danced under the lights as Alicia Keys’ “Empire State of Mind” played, then stopped near an American Eagle billboard featuring her campaign. Page Six reported that the couple rode bikes, ate burgers and took in the lights during the undercover date night.
That billboard detail gave the video its best twist. Sweeney went to Times Square as a first-time visitor, then found herself standing beneath her own ad in the middle of the tourist crush.
Us Weekly reported that Sweeney replied to Braun’s Instagram post with emojis, adding another public nod to a relationship that has become much less private in recent months.
The Outing Followed Braun’s Public Praise
The New York video arrived days after Braun spoke warmly about his relationship during an appearance on Suzy Weiss’ Second Thought podcast.
PEOPLE reported that Braun called the woman in his life “extraordinary,” “kind,” “generous,” “smart,” “real” and “down to earth,” without naming Sweeney directly in that answer. He also called the relationship “one of the biggest surprises ever.”
When asked whether he was watching Euphoria, Braun said he was “biased” and praised “an incredible performance by a certain actress.” Sweeney stars as Cassie Howard on the HBO series.
The Romance Has Become More Public
PEOPLE reported that Sweeney and Braun were casually linked in September 2025 before sources later described the relationship as more serious.
The couple made the romance more public in spring 2026. Page Six reported that Sweeney posted Stagecoach photos with Braun in May, including pictures of the two together at the festival.
The Times Square video gives the relationship another public-facing moment, but with a softer setup than a red carpet or official event. It was a late-night request, a bike ride, a burger, and a stop under the lights where Sweeney’s own campaign was already waiting for her.