Watch Harry Styles, Taylor Swift Chat Inside Event

Swift, who took home the Best Music Video award for the 10-minute version of her song “All Too Well,” supported her ex throughout the night, even giving him a standing ovation for his Best Pop Vocal Album win earlier in the evening. 

When Styles’ name was called as the winner — beating out ABBA, Adele, Coldplay and Lizzo  — the “Evermore” singer jumped to her feet and applauded the “Watermelon Sugar” crooner while wearing a big smile across her face. She was also seen dancing to his performance as “As It Was” earlier in the evening. 

Music’s biggest event seems to be a place where history repeats itself for the duo. When the England native won the award for Best Pop Vocal Album in 2021, Swift could be seen standing and clapping wildly in support. When the pair crossed paths later in the night, they took a moment to lower their COVID-19 masks and catch up. 

The Red singer and “Two Ghosts” artist first sparked romance speculation in December 2012 after they were spotted getting cozy in New York City’s Central Park. That same month, they shared a smooch in Times Square as the ball dropped on New Year’s Eve before jet-setting to visit their families for the holidays. 

While Us reported that the musicians had called it quits just one month later, Swift made headlines when she dropped her first pop album, 1989, in 2014. The record featured an array of tracks — including “Out of the Woods” and “Style” — that left people speculating she was singing about her seemingly rocky relationship with Styles.  

The Folklore songstress never officially confirmed her music was about the “Adore You” crooner, but she has heavily teased the idea. In February 2015, she told Rolling Stone that “Style” should have been titled, “I’m Not Even Sorry.’”

During an interview on The Morning Show in December 2014, the “Gold Rush” artist opened up about her inspiration behind the tracks.

“‘Style’ is actually about those relationships that are never really done,” she explained. “You always kind of have that one person who you feel like might interrupt your wedding and be like, ‘Don’t do it, we’re not over yet.’ I think everybody has that one person who kind of floats in and out of their life and the narrative is never truly over.”

The former One Direction member, for his part, shared his thoughts on seemingly being the subject of Swift’s music during his own interview with Rolling Stone years later. 

“I’m lucky if everything [we went through] helped create those songs,” he said, noting that he can’t say for sure if the songs are about him. “That’s what hits your heart. That’s the stuff that’s hardest to say, and it’s the stuff I talk least about. That’s the part that’s about the two people.”

Since their split, Swift dated Tom Hiddleston and Calvin Harris before seemingly settling down with Joe Alwyn, whom she’s been dating since 2016. Styles, for his part, has been linked to various A-list celebrities including Kendall Jenner and Olivia Wilde. The singer and the actress were together for nearly two years before their split in November 2022.