Sydney Sweeney’s First Time in Times Square Is the Most Adorably Unexpected Couple Moment of the Year
For someone whose face has been plastered across some of the most recognizable advertising spaces in the world, the fact that Sydney Sweeney had never actually set foot in Times Square feels almost surreal. Yet that is exactly the discovery that turned a quiet Saturday night into one of the most charming celebrity couple moments of the year.
The pair hit Manhattan streets after Sweeney admitted she had never visited Times Square. The ‘Euphoria’ star and the businessman were spotted going undercover to explore the bright lights of the Big Apple, with Braun documenting the entire adventure. It is the kind of spontaneous romance that plays out like a scene from a rom-com, except this one came with bikes, burgers, and a billboard.
PEOPLE reported that Sweeney and Braun were casually linked in September 2025 before sources later described the relationship as more serious, with the couple making the romance more public in spring 2026. Sydney and Scooter were first spotted together in summer 2025, when they sparked romance rumors while attending Jeff Bezos and Lauren Sánchez Bezos’ star-studded wedding. What began as a chance connection at one of the most talked-about celebrity events of last year has quietly blossomed into something that increasingly looks like the real thing.
As seen in an Instagram post from Sunday, Braun shared a video capturing the couple’s late-night outing, which kicked off with the two pedaling rented bikes through city streets. He captioned the post, “When you’re in bed at 11pm and your girl says ‘I’ve never been to Times Square….'” Both kept low profiles with coordinated disguises, with the ‘Euphoria‘ star donning a blue hoodie and black sunglasses, while Braun sported a gray hoodie and a green baseball hat.
The night had a twist that no publicist could have scripted better. Sweeney danced under the lights as Alicia Keys’ “Empire State of Mind” played, then stopped near an American Eagle billboard featuring her own campaign, going to Times Square as a first-time visitor only to find herself standing beneath her own advertisement in the middle of the tourist crush. In the clip, Braun asked the ‘Euphoria’ star how her burger was, to which she responded through bites, “It’s really good.”
The outing comes just days after Braun offered his most candid public words yet about the relationship. Speaking on The Free Press’s ‘Second Thought’ podcast, Braun described the connection without ever mentioning Sweeney by name, saying she has been “one of the biggest surprises ever.” He also weighed in on the current season of ‘Euphoria’ when asked, saying, “I am catching it. I’m biased, I like it. I think there’s been an incredible performance by a certain actress.”
According to Us Weekly, insiders have described the couple as “the real deal,” noting that they have been slowly blending their personal lives and that Sweeney appreciates Braun’s support of her projects, while Braun is invested in her career and enjoys offering feedback when asked. Among those gushing over the Times Square video in the comments was Lauren Sánchez Bezos, who played a role in bringing them together at her and Jeff Bezos’s wedding last summer.
Between the matching disguises, the midnight bike ride, and stumbling onto her own billboard like a plot twist, the night captured something that feels genuinely refreshing about this pairing. Whether you’ve been following this romance since day one or just discovered it through this video, there is something to be said about two people who can turn a spontaneous “I’ve never been to Times Square” into a memory worth sharing.
What do you think of how Scooter and Sydney are doing romance on their own terms, and does this late-night adventure change how you see them as a couple?
