Joshua Goldman
Joshua Goldman
min read · October 3, 2025 · Entertainment

Taylor Swift's Tumultuous Friendships: From Feuds to Farewells

There are several clues that Blake Lively (L, pictured in 2023) was the inspiration behind Taylor Swift's (R) new song Cancelled! off her 12th studio album The Life of a Showgirl, which drops this Friday

Taylor Swift's Tumultuous Friendships: A Rollercoaster Ride of Drama and Drama

In a world where social media reigns supreme, Taylor Swift's friendships have been under a microscope for years. From high-profile feuds to fleeting acquaintances, the pop star's relationships with her celebrity counterparts have made headlines time and again. In this exclusive exposé, we'll delve into the wild world of Taylor Swift's friendships, exploring the highs, lows, and downright dramatics that have come to define her personal life.

Katy Perry: From BFF to Feud Frenemy

In the chorus, the 35-year-old billionaire pop star sings about toxic friends who are more alike than not: 'Good thing I like my friends cancelled / I like 'em cloaked in Gucci and in scandal / Like my whiskey sour / And poison thorny flowers'

Remember when Taylor Swift and Katy Perry were the epitome of friendship? They'd regularly post adorable Instagram photos together, and it seemed like their bond was unbreakable. But behind closed doors, a very different story was unfolding. Sources close to the situation revealed that the two had been feuding over backup dancers on Taylor's 1989 tour. The tension finally boiled over in 2014, with Taylor hinting at a female "saboteur" on her Instagram account.

Fast-forward to 2017, and Katy herself confirmed the feud in an interview, stating that she was "never going to talk about" their friendship in public. Ouch! But don't worry, folks; these two have since buried the hatchet, with Taylor even inviting Katy to join her squad at the 2019 VMAs.

Jaime King: From Godmother to Ghosted

The 38-year-old Gossip Girl alum just so happened to serve as the brand ambassador for the Italian luxury fashion house's fragrance, Gucci Première, back in 2012-2013

In 2014, Jaime King and Taylor Swift seemed like an unstoppable duo. The actress was a regular fixture in Taylor's entourage, attending events and parties together. But after just two years of friendship, Jaime's appearances with Taylor began to dwindle. Sources claim that the two had grown apart, despite their initial close bond.

Jaime even went on to ask Taylor to be her son Leo's godmother in 2015 – a gesture that seemed like a testament to their enduring relationship. However, by 2020, it was clear that Jaime had been ghosted by Taylor. The actress's Instagram posts went from frequent appearances with Taylor to awkward solo shots.

Dianna Agron and Hailee Steinfeld: Brief Fling Friendships

Taylor's reference to 'whiskey sour' could easily be about Blake's liquor company Betty Booze, which manufactures three bourbon-infused canned cocktails including 'Apple Ginger Sour Cherry' (pictured in 2023)

In the early 2010s, Dianna Agron and Taylor Swift seemed like they were destined for greatness. Fans pointed out numerous references to their friendship in Taylor's Red album, leading many to speculate about a possible romance between the two.

But by 2013, rumors of a romantic relationship had begun circulating – only to be quickly debunked as unfounded gossip. The two were still spotted together at public events, but it was clear that their bond had fizzled out. Fast-forward to 2020, and Hailee Steinfeld had seemingly taken Dianna's place in Taylor's inner circle.

Hailee even shared a sweet Instagram post announcing her engagement to Josh Allen – with Taylor proudly "liking" the announcement. However, fans were quick to point out that this was an unusual move for Taylor, who is notoriously selective about her social media likes.

Swift's lyric about 'poison thorny flowers' was likely a reference to Lively's florist character, who owns a shop called Lily Bloom's in her scandal-ridden movie It Ends with Us, which is at the center of her legal war against director-leading man Justin Baldoni

Scooter Braun: The Music Mogul Who Stole Taylor's Heart (And Her Master Recordings)

In 2019, Scooter Braun made headlines when he acquired the rights to Taylor Swift's first six studio albums. The deal was worth a whopping $300 million – but came with a condition that Taylor couldn't re-record her old music.

Taylor responded by re-recording her master tracks and releasing them under the new title "Taylor's Version." But Scooter Braun didn't let it go without a fight, with his company Ithaca Holdings acquiring the catalog in 2019. It wasn't until May of this year that Taylor was able to buy back her music from Shamrock.

The problematic actress faced substantial backlash last year over how she and her husband Ryan Reynolds' company Maximum Effort marketed the domestic violence drama as she cheerfully declared: 'Grab your friends, wear your florals, and head out to see it!'

Kendall Jenner and Karlie Kloss: The Fashion Squad's Falling Out

In the mid-2010s, Kendall Jenner and Karlie Kloss seemed like an unstoppable duo on the catwalk. However, sources close to the situation revealed that their friendship had been strained for years – with Taylor Swift at the center of it all.

You see, Kendall is the half-sister of Kim Kardashian, who has long been a nemesis of Taylor's. When Karlie began spending time with Kendall in 2017, fans speculated about a possible falling out between the two supermodels and Taylor.

'Did you girl-boss too close to the sun?' the 14-time Grammy winner asked. 'Did they catch you having far too much fun? / Come with me, when they see us, they'll run / Something wicked this way comes' (pictured in 2024)

The tension came to a head when Karlie was spotted at a party hosted by none other than Scooter Braun – just weeks after Taylor had publicly feuded with the music mogul. The incident marked the beginning of the end for their friendship, with sources claiming that Karlie and Taylor "don't speak" regularly anymore.

Kanye West: The Feud That Wouldn't Die

Last but certainly not least, we have Kanye West – a man who's been at odds with Taylor Swift since 2016. The rapper's public attacks on Taylor's personal life and music were sparked by his own perceived slights against her.

When Taylor sang about 'At least you know exactly who your friends are / They're the ones with matching scars' she could've been referencing their rumored matching plastic surgery procedures

But despite their seemingly irreconcilable differences, the two have made amends in recent years. In fact, sources close to the situation claim that Kanye has even apologized for his past behavior – although Taylor's team remains tight-lipped about any possible truce.

The Verdict: Taylor Swift's Friendships Are a Messy Business

In conclusion, Taylor Swift's friendships are a wild ride – full of drama, intrigue, and more than a few surprising twists. From high-profile feuds to fleeting acquaintances, the pop star's relationships with her celebrity counterparts have made headlines time and again.

In just five months, Blake will face off against Baldoni (M, pictured in 2024) at her sexual harassment and defamation trial in Manhattan US District Court, and Swift has been begrudgingly subpoenaed but not yet deposed

But what does it all mean? Is Taylor simply a magnet for drama, or is there something more at play here? Only one thing is certain: in the world of Taylor Swift, friendships are always complicated – but rarely dull.

According to Justin's attorney Bryan Freedman (pictured February 3), Lively allegedly blackmailed the betrothed bride-to-be in February by threatening to release nine years of private text messages if she didn't issue a statement of support amid her legal war

'Did you make a joke only a man could? Were you just too smug for your own good?' Taylor sang. 'Or bring a tiny violin to a knife fight? Baby, that all ends tonight' (pictured in 2023)

The Another Simple Favor actress previously claimed Swift was involved in every aspect of It Ends with Us, including the casting of Isabela Ferrer and the licensing of her 2020 song My Tears Ricochet for the movie's soundtrack (pictured in 2023)

But in May, the Pennsylvania-born belter's rep told DailyMail.com of her subpoena: 'Taylor Swift never set foot on the set of this movie, she was not involved in any casting or creative decisions, she did not score the film, she never saw an edit or made any notes on the film, she did not even see It Ends With Us until weeks after its public release' (pictured in 2024)

However, Taylor and Blake have not been publicly pictured together since their double date with their respective spouses on October 11, 2024

At this point, it's unclear if Swift even remains a 'godmother' to three of Lively's four children as she also reportedly made her half-sister Robin Lively and her Sisterhood of the Traveling Pants castmates her kids' godmothers too

Another sign that the How Does It End singer is over the Valley Girl was the fact that the only featured guest on The Life of a Showgirl is her pop protégée Sabrina Carpenter (R, pictured in 2019), who had nothing but glowing things to say about being directed by Baldoni (L) in the 2020 Disney+ musical drama Clouds

'Every single song is on this album for hundreds of reasons. It is just right,' Taylor said on her fiancé Travis Kelce's podcast New Heights August 11. 'This album isn't really about what happened to me onstage [during my 149-date Eras Tour]. It's about what I was going through offstage. This, to me, tells more of what the actual contents lyrically of the album are'

The 12-track record reunited the How Does It End singer with producers Max Martin and Shellback, who helped mastermind her albums Red (2012), 1989 (2014), and Reputation (2017)

Swift is scheduled to appear on The Graham Norton Show this Friday (pictured Wednesday), The Tonight Show Starring Jimmy Fallon next Monday, and Late Night with Seth Meyers on October 9