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Ed Sheeran and Taylor Swift attend The 58th GRAMMY Awards at Staples Center on February 15, 2016© WireImage

Ed Sheeran shares incredibly rare pictures of Taylor Swift with ex-boyfriend and former friends

Ed and Taylor have been friends for almost 15 years

Rebecca Lewis
Rebecca Lewis - Los Angeles
Los Angeles correspondentLos Angeles
May 1, 2025
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Ed Sheeran released his new single "Old Phone" on May 1 and in honor of the moment has turned his phone back on, almost 10 years after famously turning it off, and shared a series of incredibly rare pictures that were sitting in the gallery.

Louis Tomlinson, Ed Sheeran, Calvin Harris, Taylor Swift and Niall Horan pose backstage at Billboard Awards© Ed Sheeran

One of the pictures, shared on a new Instagram account, was of Taylor Swift in 2015 with her then-boyfriend Calvin Harris at that year's Billboard Awards with Louis Tomlinson and Niall Horan of One Direction.

"2015 billboard awards. I'm dribbly drunk at this point," he captioned the post, which saw fans of Ed, Taylor, Calvin and One Direction thank him for the throwback.

2013 THROWBACK

Picture taken by Ed Sheeran of Taylor Swift and Hailee Steinfeld on a beach in RI© Ed Sheeran

Other pictures he posted included from what appeared to be in 2013 when he supported Taylor on the Red tour, and they took a "mid tour beach trip" to Rhode Island, where the same year she purchased Holiday House in the coastal town of Westerly.

The snap showed Taylor walking with Hailee Steinfeld, whom she was friendly with for several years, on the beach as another friend walked ahead and took their picture.

Ed took the snap from behind.

Taylor Swift holds two slices of pizza in a pizzeria © Ed Sheeran

"Getting pizza somewhere on tour," read the caption of another picture, which showed Taylor holding up two slices of cheese pizza from a local pizzeria in Westerly, as Hailee sipped on a soda next to her.

Ed Sheeran and Taylor Swift take a selfie circa 2013© Ed Sheeran

Other snaps included a selfie the pair took, and Ed spending time with old school friends.

Ed and Taylor became friends when he moved to Nashville in 2011 and she covered his song "The A Team" on tour. They collaborated on her 2012 album Red, and he then joined her on the tour the following year.

LONGTIME BFFS

Taylor Swift and Ed Sheeran perform onstage during Z100's Jingle Ball 2012, presented by Aeropostale, at Madison Square Garden © Theo Wargo

In 2016, Taylor paid tribute to the singer on his birthday writing: "Looking back on the highlights of my life, there's a moment I'll never forget from a day in London about two years ago. I was in town to play the O2 and I was out shopping on my day off.

"My friend Ed Sheeran met up with me in this little shop where I was buying ballet shoes. He walks in and says, 'You have to hear this new song. I think it's the best one I've ever written.' And then, as usual, he pulls out his phone and gives me headphones. I sat there on a bench in that store and heard "Thinking Out Loud" for the first time, as little kids were picking out tutus and leotards next to us."

She continued: "Little did we know it would go on to be first dance song at countless weddings all over the world, become Ed's biggest hit, and eventually go on to win him Song of the Year at the 2016 Grammys."

NFL WAGS

josh allen holding hands hailee steinfeld nfl honors© Getty Images

Actress Hailee was a member of Taylor's early squad, with the pair meeting in 2010 after being introduced by mutual friend Emma Stone.

They grew apart over the years although their paths almost crossed several times in recent years as Taylor is dating NFL player Travis Kelce and Hailee is engaged to Buffalo Bills quarterback Josh Allen.

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