Taylor Swift – Should’ve Said No

The lyrics of Taylor Swift’s “Should’ve Said No” speak about the pain caused by a cheating partner. It is also a breakup song themed on the rash action taken by the singer’s former partner.

The singer begins by reminiscing on their beautiful memories, of which she employs metaphors such as songs, flowers and smiles to describe. Her point however is that, he has thrown all that away following her discovery that he cheated on her. Although Taylor does not clearly mention how he cheated, we can deduce from the mention of weakness and other terms that he may have had a sensual affair with another girl. The singer is particularly mad because she believes that he should have never allowed himself to be in such a vulnerable position. She is also of the view that he should have thought about her first before cheating, instead of hurting her and later coming to apologize.

Throughout the song, Swift makes it clear that she is not giving her partner another chance. To her, every ounce of trust in the relationship has been broken because of his cheating. Taylor is also suggesting that if she were in his shoes, she would have never let that happen, because she would have considered how it will affect their relationship and remained faithful. She believes that this affair was not worth breaking a beautiful relationship, and if he had simply disciplined himself and said no, all these problems would have been avoided.

Inspiration behind “Should’ve Said No”

“Should’ve Said No” is said to have been inspired by Taylor’s high school boyfriend, Sam Armstrong, who also claimed via a tweet that he and Taylor dated once again after this cheating incident. Although the artist has not specifically named Sam as the subject, she has confirmed that the song was a real account of a guy she perceived should’ve never cheated on her. She essentially based the song on the essence of saying no at the perfect time to avoid bigger problems.

Lyrics of “Should’ve Said No”


“Should’ve Said No” deeply captures the heartbreak felt after a romantic partner cheats. It also seeks to highlight the importance of individual self-discipline and the amount of trouble one can avoid through it.

Facts about “Should’ve Said No”

“Should’ve Said No” was written by Taylor Swift, who was very much a teenager when she penned it. And as a further testament to her talent, she wrote the song just a week before the recording of her debut album, “Taylor Swift”, was completed.

Big Machine Records released this track as part of that album on 24 October 2006. And later they also later reissued it as the fifth (and last) single from “Taylor Swift”.

Nathan Chapman produced this track, as he did practically the entire album.

“Should’ve Said No” topped Billboard’s Hot Country Songs listing. And outside of the US, where it has been certified Platinum, it also charted in Canada and New Zealand.

Additionally this track won a couple of BMI Awards in 2009, one in the category of Publisher of the Year and the other Award-Winning Songs.

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