Taylor Swift Songs About Her Ex-Boyfriends

In the episode, the host explores the inspiration behind Taylor Swift's songs, detailing her relationships with various exes and how they influenced her music. The narrative begins with her high school boyfriend Drew Dunlap, inspiring "Tim McGraw," and moves through a series of relationships including Sam Armstrong, who cheated on her, leading to "Should've Said No," and Joe Jonas, who ended their relationship with a brief phone call, prompting "Forever and Always." Other relationships analyzed include her almost-relationship with Martin Johnson inspiring "Love Story," her emotional connection with Stephen Barker Lyles from "Hey Stephen," and the public fallout with John Mayer after "Dear John." The host also touches on her relationships with Jake Gyllenhaal, associated with the song "All Too Well," and Harry Styles, who inspired "Style." Taylor's songs also reflect on her relationships with Calvin Harris, Tom Hiddleston, and Joe Alwyn, highlighting how her personal experiences deeply inform her songwriting and contribute to her artistic expression.

• "Tim McGraw" is about Taylor Swift's first high school boyfriend, Drew Dunlap.
• The song idea originated in math class, thinking about things that would remind him of her.
• Taylor Swift wrote the song with Liz Rose quickly after school.

The idea for this song came to me in math class I just started singing to myself when you think Tim McGraw was dating a guy who moved away and it was going to be over for us.

This quote explains the emotional context and inspiration behind the song "Tim McGraw," reflecting on a relationship that was coming to an end due to distance.

• "Should Have Said No" is about Taylor Swift's sophomore boyfriend, Sam Armstrong, who cheated on her.
• The song expresses a refusal to forgive and a lament over the lost relationship.
• Sam Armstrong sought fame by revealing their past relationship online.

Taylor was 16 when she wrote should have said no it's about her sophomore boyfriend Sam Armstrong who cheated on her while she was on radio tour in summer 2006.

This quote provides the background story for "Should Have Said No," highlighting the emotional betrayal Taylor Swift experienced due to cheating.

• "Come in With the Rain" was written by Taylor Swift after she ended the relationship with Sam Armstrong.
• The song conveys skepticism towards apologies and the pain of disappointment.

What if I told I dated her come in with the rain she wrote it when she was 16 years old about Sam after she dumped him.

This quote indicates that "Come in With the Rain" was a response to the end of their relationship, capturing the emotional aftermath of the breakup.

• "Love Story" is speculated to be about Martin Johnson from Boys Like Girls.
• Taylor Swift related the song to Romeo and Juliet due to her family's disapproval of him.
• Andrea Swift confirmed the family's strong disapproval of the relationship.

Love story is actually about a guy that I almost stated but when I introduced him to my family and my friends they all said they didn't like him.

The quote explains the real-life parallel to "Love Story," where Taylor Swift faced family opposition to a romantic interest, similar to the narrative of Romeo and Juliet.

• "Hey Stephen" was inspired by Stephen Barker Liles, whom Taylor Swift dated.
• They formed a close bond while touring together.
• The hidden message in the album booklet hinted at their relationship.

Stephen Barker Lyles is one of Taylor's Exes who who inspired the song. Hey Stephen he's in a country band called love and theft.

This quote reveals the personal connection behind "Hey Stephen," linking the song to a romantic interest Taylor Swift had while on tour.

• "Forever and Always" was written about Joe Jonas and their fading relationship.
• Taylor Swift felt confused and frustrated as she noticed a change in the relationship.
• She publicly addressed the breakup on the Ellen show, which was seen as a rebellious act.

Forever and always is a song written for Joe Jonas who she was dating at the time.

This quote summarizes the emotional turmoil Taylor Swift experienced in her relationship with Joe Jonas, which inspired "Forever and Always."

• "Back to December" is an apology to Taylor Lautner for Taylor Swift's carelessness.
• Lautner is aware that the song is about him.
• The song references a painful incident involving Kanye West at the VMA awards.

Back to December is a song off the album speak now. and it's about Taylor looking back at her relationship with Taylor Lautner and apologizing.

This quote clarifies that "Back to December" is an expression of regret towards Taylor Lautner, making it unique as an apologetic song in Taylor Swift's discography.

• Fans believe "Midnight Rain" may also be about Taylor Lautner.
• The song contrasts their different desires and life paths.
• References to their relationship are found within the lyrics.

Swifties consider him their favorite Taylor's ex cause he was sunshine I was midnight rain.

The quote suggests that "Midnight Rain" reflects on the differences between Taylor Swift and Taylor Lautner, using metaphorical language to describe their relationship dynamic.

• "Dear John" addresses a relationship with an older individual and the complexities involved.
• The song criticizes the imbalance of power and emotional manipulation.

• Taylor Swift's song "Dear John" is perceived as humiliating by John Mayer.
• Mayer felt the song was undeserved and a "lousy thing" for Swift to do.
• Swift expresses regret about dating an older man and being naive.
• Mayer responded with a song titled "Paper Doll," which references Swift's song "22."
• Fans speculate that Swift's song "Would've, Could've, Should've" and "Tolerate It" are about her relationship with Mayer.

"John Mayer stated that he was humiliated by the song Dear John it made me feel terrible because I didn't deserve it mayor said for Rolling Stone it was a really lousy thing for her to do."

This quote reflects John Mayer's feelings of humiliation and undeserved treatment due to Taylor Swift's song "Dear John," which he perceived as a personal attack.

• "All Too Well" is a fan-favorite song and has a short film.
• The song details her relationship with Jake Gyllenhaal.
• Swift uses a scarf as a metaphor, possibly for virginity.
• Gyllenhaal believes the song is about Swift's relationship with her fans.
• "The Moment I Knew" is about Gyllenhaal not showing up for Swift's birthday.
• "State of Grace" and "I Bet You Think About Me" are also believed to be about Gyllenhaal.

"All Too Well became one of the Swifty's most beloved tracks it is the fandom's Anthem a 10-minute song with a 14-minute short film gives us a glance into Taylor's relationship with Jake."

This quote describes the significance of "All Too Well" for Taylor Swift's fans and its connection to her past relationship with Jake Gyllenhaal.

• Swift's song "Starlight" is inspired by Ethel and Robert F. Kennedy.
• Swift wrote the song after seeing a picture of the Kennedys dancing.
• She dated Conor Kennedy and wrote "Begin Again" about their relationship.
• The song "Style" is a clear reference to Harry Styles due to specific descriptions.
• "Out of the Woods" and "Style" from the album 1989 are rumored to be about Styles.

"Taylor was dating Robert Kennedy's son Connor Kennedy in 2012.. the two of them were showing major PDA on the Kennedy Compound in Hyannis Port Massachusetts."

This quote provides context for Taylor Swift's relationship with Conor Kennedy and how it influenced her songwriting, specifically the song "Starlight."

• The scarf in "All Too Well" symbolizes something precious, possibly virginity.
• Swift's lyrics often include metaphors and symbolic references to personal experiences.
• Fans and media speculate about the real-life inspirations behind her songs.

"but Taylor said in a conversation with Tiff that the scarf is a metaphor and it probably means a metaphor for virginity when I say it's a metaphor I'm just gonna stop leave it."

This quote emphasizes Taylor Swift's use of metaphors in her songwriting, with the scarf from "All Too Well" serving as a prominent example of her symbolic language.

• Taylor Swift discusses the creative process and inspiration behind her songwriting.
• Harry Styles is mentioned as both a source of inspiration and as a fellow artist who writes from personal experience.
• Taylor acknowledges the impact of her relationships on her songwriting.

"I write from my own experience Harry said everyone does so."

This quote highlights the personal nature of Taylor Swift's songwriting, which is influenced by her own life experiences, as is the case with many artists including Harry Styles.

• Taylor Swift's songs often reflect her past relationships, with some tracks rumored to be about her ex-boyfriend Harry Styles.
• Songs like "I Know Places," "I Wish You Would," "Clean," "This Love," and "How You Get the Girl" are speculated to be inspired by her relationship with Harry.
• Harry Styles wrote "Perfect" while in One Direction, which is believed to be about Taylor Swift.

"Harry even wrote a song about Taylor while he was still in One Direction it's called perfect and the lyrics go..."

This quote indicates that not only does Taylor Swift write about her relationships, but her relationships also inspire music from her ex-partners, such as Harry Styles' song "Perfect."

• Taylor Swift and Calvin Harris's relationship and breakup are discussed.
• The song "Getaway Car" is speculated to describe Taylor's departure from her relationship with Calvin Harris, using Tom Hiddleston as a metaphorical "getaway car."
• Calvin Harris's response through music is noted, with references to his song that includes lyrics believed to be about Taylor Swift and Tom Hiddleston.

"Calvin strikes back he wrote and produced songul for John Newman he even referenced Tom's most famous character Loki from Thor with the lyrics..."

This quote suggests that Calvin Harris used his music to express his feelings about the end of his relationship with Taylor Swift, including references to Tom Hiddleston, whom Taylor was seen with shortly after.

• Taylor Swift's music often encapsulates her personal growth and changes in her life.
• The song "I Forgot That You Existed" from the album "Lover" is rumored to be about her moving on from Calvin Harris.
• Lyrics from the song reflect Taylor's feelings of liberation and indifference towards an ex.

"I forgot that you existed was released on the album lover in 2019. and it's rumored to be about Calvin..."

The quote implies that Taylor Swift's song "I Forgot That You Existed" is a representation of her emotional detachment from her past relationship with Calvin Harris.

• Taylor Swift's multi-year relationship with Joe Alwyn is highlighted.
• The relationship has been a significant source of inspiration for many songs across different albums.
• Songs from the "Reputation" album, such as "Ready for It" and "End Game," are noted for their references to Joe Alwyn.
• Lyrics from various songs depict the depth of their relationship and the impact of Joe's support during difficult times.

"Joe is the one that loved her when her reputation was at its lowest..."

This quote emphasizes the importance of Joe Alwyn's support to Taylor Swift during a challenging period in her career, which is reflected in her music.

• Taylor Swift's songs convey themes of love, commitment, and the desire for a lasting relationship.
• The album "Lover" is particularly focused on her relationship with Joe Alwyn.
• Lyrics from songs like "Cornelia Street," "Paper Rings," and "New Year's Day" express her deep feelings and commitment to Joe.

"Most of the songs on the album lover released in 2019 are about Joe."

The quote indicates that the album "Lover" is predominantly inspired by Taylor Swift's relationship with Joe Alwyn, showcasing her feelings and commitment through her songwriting.

• Taylor Swift expresses her love for a London boy and enjoys walking in Camden Market.
• She feels a significant change in her life, comparing it to emerging from a long darkness into daylight.
• The lyrics suggest a deep intertwining of lives and a shift from seeing love in black and white to golden.

I love a London boy I enjoy walking Camden Market in the afternoon... I've been sleeping so long in a 20-year dark night. and now I see daylight I only see daylight.

This quote demonstrates Taylor's affection for someone from London and the transformative experience of love, which has brought light into her life.

• "Folklore" was released in 2020, with some songs co-written by Joe.
• The songs "Exile" and "Betty" are highlighted as collaborations.
• Taylor Swift mentions this is the first album where she let go of the need for the songs to be 100% autobiographical.

Taylor released folklore in 2020 and some of the songs were crew written by Joe... This was the first album where I've ever let go of that need to be 100 autobiographical.

The quote outlines the release of "Folklore" and the collaborative effort with Joe, signaling a departure from Taylor's usual autobiographical songwriting approach.

• "Peace" is about Taylor Swift's struggle to balance public and private life while in a relationship with Joe.
• The song reflects on the authenticity of love and the sacrifices made for it.

Peace was about trying to find a balance between her being a public Persona and her private life while she was falling in love with Joe.

This quote explains the song "Peace" as a narrative of Taylor Swift's efforts to maintain equilibrium between her public image and her personal relationship with Joe.

• Taylor Swift uses the metaphor of an "Invisible String" to describe the serendipitous connection to Joe.
• She recalls specific details such as the color of Joe's shirt and their memories in LA.

Teal was the color of your shirt when you were 16... isn't it just so pretty to think all along there was some Invisible String tying you to me.

The quote captures the intimate and fated nature of Taylor Swift's relationship with Joe, using personal memories and the concept of an "Invisible String" that connects them.

• Joe co-wrote "champagne problems," "Coney Island," and the title track "Evermore" on Taylor Swift's second 2020 album.
• He is credited under the pseudonym William Bowery.
• The lyrics of "sweet nothing" suggest a theme of finding solace and peace in their relationship.

Joe helped co-write champagne problems, Coney Island, and title track. Evermore... William Bowery is listed in songwriting credits for sweet nothing.

This quote highlights Joe's involvement in the creation of "Evermore" and his contribution to the song "sweet nothing," which reflects on the comfort found in their relationship.

• Taylor Swift reveals her strategic approach to winning Joe's affection in "Mastermind."
• The song describes a mutual realization of their feelings for each other.

So I told you none of it was accidental... you knew the entire time you knew that I'm a mastermind.

The quote from "Mastermind" discloses Taylor Swift's intentional efforts in the early stages of her relationship with Joe and the shared acknowledgment of their connection.

• Taylor Swift compares falling in love to the unusual phenomenon of snow falling on a beach.
• The song captures the surreal and unexpected nature of two people falling in love simultaneously.

Are we falling like snow at the beach... is this real is this a dream is this for real.

This quote uses the metaphor of snow on a beach to describe the rare and magical moment when two people realize they are in love at the same time.

• Taylor Swift thanks Joe's exes for shaping him into the person she loves.
• She appreciates the past experiences that led Joe to her.

All of the girls You Loved Before made you the one I've fallen for.

Taylor Swift's gratitude towards Joe's past relationships is expressed in this quote, acknowledging their role in his personal development.

• The song "Lavender Haze" is about Taylor Swift's six-year relationship and the desire to stay within the blissful state it provides.
• She mentions the need to ignore external rumors and tabloid stories to protect the genuine aspects of her relationship.

Like my relationship for six years we've had to dodge weird rumors tabloid stuff... and so this song is sort of about the act of ignoring that stuff to protect the real stuff.

Taylor Swift discusses the challenges of public scrutiny and the importance of focusing on the true substance of her relationship, as described in the song "Lavender Haze."

• Taylor Swift's song "Hits Different" details the emotional impact of her breakup with Joe Alwyn.
• She contrasts this breakup with past relationships, emphasizing its unique pain.

After her recent split with Joe Alwyn Taylor released a song called hits different... it hits different cause it's you.

The quote reveals the depth of Taylor Swift's feelings regarding her breakup with Joe Alwyn and how it has affected her differently than previous relationships.

• "You're Losing Me" explores the realization that the relationship is ending.
• Taylor Swift reflects on the inability to save the relationship and the pain of potential loss.

You're losing me. I can't find a pulse my heart won't start anymore for you cause you're losing me.

This quote from "You're Losing Me" conveys the heartbreak and resignation Taylor Swift feels as she recognizes the dissolution of her relationship with Joe.

• Taylor Swift acknowledges the connection between her breakups and her art.
• She hints at the anticipation for her next album, suggesting it will be influenced by her personal experiences.

If it weren't for these breakups we wouldn't have this art... we already know her next album is going to be fire.

Taylor Swift's quote reflects on the inspiration drawn from her breakups for her songwriting and teases the potential emotional depth of her upcoming album.