Ellen DeGeneres once asked Taylor Swift about 'Dear John' and things got awkward: "Is this song..."

Taylor Swift struggled to answer Ellen DeGeneres' awkward questions on live TV and we totally get why
PUBLISHED MAR 30, 2025
A screenshot of Taylor Swift and Ellen DeGeneres from an interview on 'The Ellen DeGeneres Show' (Cover Image Source: YouTube | The Ellen Show)
A screenshot of Taylor Swift and Ellen DeGeneres from an interview on 'The Ellen DeGeneres Show' (Cover Image Source: YouTube | The Ellen Show)

Once a prominent name in the talk show arena, Ellen DeGeneres may have bid farewell to her illustrious Hollywood career, but her past controversies do not seem to cool off. DeGeneres, who recently relocated to England, severing all ties with the entertainment industry, is once again grabbing massive attention for her uncomfortable questioning and this time it involved Taylor Swift. While the exchange was certainly awkward, kudos to Swift for handling the situation with grace. 

NEWARK, NEW JERSEY - AUGUST 26: Taylor Swift attends the 2019 MTV Video Music Awards at Prudential C
Taylor Swift attends the 2019 MTV Video Music Awards at Prudential Center on August 26, 2019, in Newark, New Jersey (Image Source: Getty Images for MTV | Photo by Jamie McCarthy) 

During her 2010 appearance on 'The Ellen DeGeneres Show,' the host brought up Swift’s reputation for writing about her relationships, as per The Things. DeGeneres playfully suggested that the men Swift had dated might be afraid to be near her because of what she might write about them. She asked, "Do you write about your experiences?" "That seems to be the pattern, yeah," Swift responded when asked if she often writes about her relationships.



 

Soon, things became awkward when DeGeneres brought up Swift's song 'Dear John' from her 'Speak Now' album. The host asked about the speculation that it was about singer John Mayer, saying, "Is this song about him? I mean, it could just be a Dear John song." Before a long pause, Swift said, "It could be." The silence caused the audience to laugh, and she added, "That song kind of is what it is," to which DeGeneres said, "Okay, great. We know the answer now. It's about him." When Swift playfully made a shocked face, DeGeneres continued, "Well, you didn't dispute it, so obviously..." to which Swift replied, "I guess people are going to continue to speculate about it, and I'm going to continue to never tell them who the song is about." However, DeGeneres did not stop and said, "Right, but it's about him." 



 

For context, both Swift and Mayer were reportedly linked in 2009 when they collaborated on 'Half of My Heart,' as per People. The two singers performed together multiple times, thus fueling romance rumors after Swift's split from Taylor Lautner. Although the duo never publicly confirmed their relationship, both later released breakup songs, with Swift's 'Dear John' and Mayer's 'Paper Doll' widely believed to reference their brief romance, which ended in 2010.



 

While Swift has mostly avoided addressing the speculations around 'Dear John,' she recently acknowledged fan speculations during her Eras Tour stop in Minneapolis on June 24, 2023, as reported by Bustle. The 'Bad Blood' singer performed the song as one of her secret songs at the US Bank Stadium. Swift also addressed the re-release of 'Speak Now' (Taylor’s Version), stating, "I'm 33 years old. I don't care about anything that happened to me when I was 19... I'm not putting this album out so you can go on the internet and defend me against someone you think I wrote a song about 14 million years ago."



 

Swift further said, "I'm putting this album out because I want to own my music and I believe any artist who has a desire to own their music should be able to." In a 2012 interview with Rolling Stone, Mayer also shared his thoughts on the songs. The singer said, "I never got an email. I never got a phone call. I was really caught off-guard, and it really humiliated me at a time when I'd already been dressed down. I mean, how would you feel if, at the lowest you've ever been, someone kicked you even lower?" 

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