In a heartfelt and nostalgic moment for fans, Ed Sheeran has turned heads by unveiling a treasure trove of rare, behind-the-scenes photos featuring Taylor Swift , her ex-boyfriend Calvin Harris , and former close friends like Hailee Steinfeld . The photos, shared through a new Instagram account, celebrate the release of his latest single, Old Phone, and mark a symbolic return to digital life for the singer, who famously turned his phone off nearly a decade ago.
Ed Sheeran surprises fans with rare behind-the-scenes photos of Taylor Swift and Calvin Harris
One of the standout images features Taylor Swift with Calvin Harris at the 2015 Billboard Music Awards, alongside Louis Tomlinson and Niall Horan of One Direction. Ed, clearly in high spirits, captioned the photo with: “2015 billboard awards. I'm dribbly drunk at this point.” The candid post quickly went viral, delighting fans of all four artists with its raw, unfiltered glimpse into a star-studded night.
Another emotional highlight was a photo taken during Taylor’s Red Tour in 2013, when Ed supported her across several stops. The picture captures Taylor walking along a Rhode Island beach with actress Hailee Steinfeld, part of Taylor’s once-iconic “squad.” Ed, who took the photo from behind, called it a “mid tour beach trip”—likely referencing the early days of Taylor’s ownership of the now-famous Holiday House in Westerly.
Sheeran also shared an image of Taylor holding up two slices of cheese pizza in a local Westerly pizzeria, with Hailee sipping soda beside her. Captioned, “Getting pizza somewhere on tour,” it offered a glimpse into the everyday, carefree moments of their friendship. Other pictures included a 2013-era selfie of Ed and Taylor, and shots of Ed reconnecting with his school friends, adding a personal layer to the nostalgic collection.
Ed and Taylor’s friendship began in 2011 when Taylor covered “The A Team” and invited him to join her Red Tour. Taylor later shared a touching memory from 2014: “I sat there on a bench in that store and heard ‘Thinking Out Loud’ for the first time… Little did we know it would go on to be first dance song at countless weddings all over the world.”
Also Read: Backup dancer for Taylor Swift now? Travis Kelce’s golf dance with Justin Timberlake sparks backlash and Swiftie praise
Their enduring friendship, captured through Ed’s lens, reminds fans not only of iconic pop culture moments but also of the deep connections behind the music they love.
Ed Sheeran surprises fans with rare behind-the-scenes photos of Taylor Swift and Calvin Harris
One of the standout images features Taylor Swift with Calvin Harris at the 2015 Billboard Music Awards, alongside Louis Tomlinson and Niall Horan of One Direction. Ed, clearly in high spirits, captioned the photo with: “2015 billboard awards. I'm dribbly drunk at this point.” The candid post quickly went viral, delighting fans of all four artists with its raw, unfiltered glimpse into a star-studded night.
📸 | New (old) Taylor Swift content from Ed Sheeran on Instagram
— Taylor Swift Updates (@tswiftscoop) April 29, 2025
—Via @/teddysoldphone pic.twitter.com/4HMPInhQ83
Another emotional highlight was a photo taken during Taylor’s Red Tour in 2013, when Ed supported her across several stops. The picture captures Taylor walking along a Rhode Island beach with actress Hailee Steinfeld, part of Taylor’s once-iconic “squad.” Ed, who took the photo from behind, called it a “mid tour beach trip”—likely referencing the early days of Taylor’s ownership of the now-famous Holiday House in Westerly.
Sheeran also shared an image of Taylor holding up two slices of cheese pizza in a local Westerly pizzeria, with Hailee sipping soda beside her. Captioned, “Getting pizza somewhere on tour,” it offered a glimpse into the everyday, carefree moments of their friendship. Other pictures included a 2013-era selfie of Ed and Taylor, and shots of Ed reconnecting with his school friends, adding a personal layer to the nostalgic collection.
Ed and Taylor’s friendship began in 2011 when Taylor covered “The A Team” and invited him to join her Red Tour. Taylor later shared a touching memory from 2014: “I sat there on a bench in that store and heard ‘Thinking Out Loud’ for the first time… Little did we know it would go on to be first dance song at countless weddings all over the world.”
Also Read: Backup dancer for Taylor Swift now? Travis Kelce’s golf dance with Justin Timberlake sparks backlash and Swiftie praise
Their enduring friendship, captured through Ed’s lens, reminds fans not only of iconic pop culture moments but also of the deep connections behind the music they love.
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