Music manager Scooter Braun and actress Sydney Sweeney spent Sunday, May 31, 2026, on an undercover date in New York City's Times Square [1], [2].

The outing highlights the couple's public relationship and the influence of social media in crafting celebrity narratives through curated, "impromptu" experiences.

The pair documented their trip in an Instagram Reel, which showed them riding Citi Bikes and exploring the tourist hub together [1], [2]. Braun said the trip was sparked by a late-night conversation. "When you're in bed at 11 p.m. and your girl says 'I've never been to Times Square'," Braun said [1].

Sweeney expressed surprise at her previous lack of familiarity with the landmark. "I can't believe I've never been to Times Square before," Sweeney said [1]. The visit was framed as her first time experiencing the area [1].

However, subsequent reports have challenged the claim that the actress was a first-time visitor. A report published on June 1, 2026, stated that Sweeney actually visited Times Square with a male co-star in 2023 [3].

The discrepancy between the couple's social media presentation and previous sightings suggests the "first-time" narrative may have been a plot point for the video content. Despite the contradiction, the couple continued their outing through the city streets, attempting to remain low-profile while filming [1], [2].

“"I can't believe I've never been to Times Square before."”

This incident illustrates the gap between a celebrity's curated social media persona and their actual history. By framing a common tourist destination as a novel experience, the couple created a romantic narrative for their followers, even though public records or previous sightings contradict the claim.