9: “Ruin the Friendship” — the price of playing it safe

“Ruin the Friendship” expands on the vulnerability we saw in “Eldest Daughter” and reveals the showgirl at her most human.

In this episode, we unpack the song’s quiet heartbreak and the recurring tension between the “good girl” who plays it safe and the artist who longs to live boldly. We’ll trace how Swift’s lyrics move through time, how regret becomes revelation, and how this moment of tenderness deepens the album’s larger story.

Don’t miss the writing prompts at the end, or go to www.maraeller.com/prompts to get them sent straight to your inbox.

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Transcript

0:04

Welcome to Lit one 12, the Life of a Showgirl where we treat Taylor Swift's latest album like a novel I'm your host, Mara Eller, a literature and writing teacher with 16 years of experience at the high school and college level. I just retired to focus on editing and book coaching, but when I started getting requests for this series on social media, I couldn't resist. Whether you're a veteran swifty or just an AP lit nerd like me who happens to like her music, all are welcome here. I've even got something for you writers, creative prompts inspired by the subject of each lesson. You can find them at the end of the episodes. So grab your metaphorical notebook and let's unpack this record together, chapter by chapter, song by song. Anyone remotely familiar with Taylor Swift's repertoire knows she's written more than a few breakup songs, but with ruin the Friendship, she flips the script. In this song, her biggest heartbreak isn't a love that ended but one that never began. The title sounds bold, almost reckless, but the song itself is introspective, tender, full of longing and regret. It's not about destroying a friendship. It's about regretting that you didn't take the risk that might have deepened it into something more. The song is built around a single refrain should have kissed you. Anyway, the chorus becomes a mantra about action versus hesitation revolving around the single truth. It's better to take the risk than to live with regret. In the final bars of the song, she makes it clear. My advice is always ruin the friendship. Better that than regret it for all time. My advice is always answer the question better that than ask it all your life. She's not actually encouraging anyone to ruin a friendship. She's saying, better take the risk and find out because what if it's good? That's advice for love, but also for life more broadly. It's about daring to be vulnerable to risk, rejection, heartbreak, embarrassment to live boldly rather than perfectly Musically, this song strips away the showgirl persona we see in other tracks. It starts out with drums reminiscent of the opening line to Lenny Kravitz's Followed by a prominent electric baseline and some simple guitar. It's been described as having a 1980s soft rock vibe with some nineties country influences. It gives it a nostalgic wistful feel, and that continues for the full track. unlike the other songs on this album, there are no showgirl flourishes. The message is that there's no spectacle here, just introspection, regret, and longing. This track follows eldest daughter, where we also saw her reflecting on her childhood, on what she may have lost by choosing this showgirl life. But now the focus is on her adolescence and it takes us even deeper into the girl behind the mask. The lyrics give us some of that classic Taylor Swift songwriting Where the narrative travels through time. Each chorus adding something to the previous one until we get a dramatic, and in this case, heartbreaking reveal. In the final chorus, she sings about three specific moments when she wanted to kiss a person in high school, narrating them from the perspective of her adult self. Looking back with regret regret, that becomes even more poignant in the final chorus Where she's attending his funeral. It seems very likely that the song was inspired by Taylor's high school friend, Jeff Lang, who died in 2010 at just 21 years old. Taylor flew home for his funeral the day before accepting the songwriter of the year award. so who is the showgirl singing to? I tend to interpret this song as though the showgirl is still in the low that followed her father figure victory that we discussed in the previous lesson about eldest daughter In that song, she was singing about internet haters and her concerns about losing her humanity, losing her ability to be loyal, and then suddenly she finds out her friend from high school died, and it brings up all of these memories and feelings of sadness. Our showgirl has been asking a lot of what if questions about the future. What if I end up alone? What if I lose it all? Now she's asking what if about the past? What if I'd chosen a different path back in high school? What might I have missed out on? Her regret is focused on this acutely tragic example, the friend from high school whom she wanted to kiss and didn't, but it has implications for life more broadly. What else might I have missed because I wanted to play it safe? She seems to be asking verse one. Glistening grass from September. Rain gray overpass full of neon names. You drive 85 Gallatin Road on the Lakeside Beach. These are places in Tennessee where Taylor went to high school for a time, and I think this is a really great example of Taylor's songwriting skill. She's using imagery and detail, really specific detail, to immerse us in a particular moment in time. She continues, watching the game from your brother's Jeep. It's not just watching the game or even watching from a car, but from your brother's Jeep. That specificity is what really brings it to life. Your smile miles wide. She uses hyperbole here, which is exaggeration for rhetorical effect. In order to emphasize how big this smile was, it indicates this person's intense happiness, but also her perception of his smile, that it was immense for her. That this is one of the clearest images in her mind from that night shows she was really paying attention to him. I imagine her feeling happy simply because of seeing him smile so big, like she's really tuned into his emotions. It's also worth noting here that. At the end of each part of the verse, like miles wide, her voice goes down to quite a low chesty voice that is, showing impressive range. I think it's like the D below middle C or something like that. So got some, uh, singing talent on display here for us. Then we come to the chorus and it was not an invitation. Should have kissed you anyway And it was not convenient, but your girlfriend was away. Should have kissed you. Anyway, I read it as her knowing that his smile wasn't an invitation for her to kiss him, but It made her want to and that she didn't. Your girlfriend was away. I imagine that maybe she didn't get to spend a lot of time with this guy because his girlfriend didn't like it, Was maybe suspicious, with good reason. But she was away on this particular day, so they had this special time together that was perhaps rare for them. It was a chance to make a move, but she doesn't. Here we start to see the tension that underlies this song and makes it much more impactful than simply, oh, I wish I'd kissed someone. The question is, why didn't she? So we start to see this tension that she's pulled between opposing forces, self-control versus desire, safety versus risk. Kissing someone who has a girlfriend is not something a good girl does. Verse two takes us into the second memory, another time when she thought about kissing him Shiny wood floors underneath my feet. Disco ball makes everything look cheap. Have fun. It's prom. again, she uses those specific sensory details to immerse us. This time in the gym for prom. She doesn't say that it's a gym, but we intuit that from the shiny wood floors. I think disco ball here is possibly a reference to her song, where Taylor wrote about being a pathological people pleaser. In this song, she says that the disco ball made everything look cheap. So maybe she's saying her tendency to do what she thinks other people want has cheapened her life, has robbed it of some beauty. When it says Have fun, I picture that as grownups telling them to have fun, like have fun. It could also imply that she wasn't really having fun. Like why include that detail? wilted corsage dangles from my wrist. This is an interesting line because again, it's a really specific, vivid piece of imagery and wilted is reminiscent of the line withered under bright lights that we had from Elizabeth Taylor, but now it's wilted under the disco ball. So it implies maybe that the guy she's dancing with wilted, like his affection dried up and maybe does she wonder if the you in this song would've wilted too? You know, since in Elizabeth Taylor, everyone withered under the bright lights, maybe this guy would've wilted under the bright lights had they actually ended up together. Not that she was thinking that at the time when she was at prom, but the older self looking back might wonder. Over his shoulder, I catch a glimpse. So she's dancing with a different guy. Presumably she went to prom with this other guy, not the one she's singing to in the song and see you're looking at me. So she's looking over her date's shoulder and she sees this other guy looking at her instead of the person he's dancing with. So they're both looking at each other instead of looking at their dates. It's such a poignant moment of them both thinking about the other, but dancing with someone else really physically embodying this gulf between them that they knew could be closed so easily. Which begs the question again. Why not? Why not kiss, connect, confess their feelings. If they have this moment of both, pretty much knowing that it's mutual, why didn't they ever act on it? Then the chorus, but it's a little different this time. And it was not an invitation, but as the 50 cent song played should have Kissed You anyway. Why 50 cent song? Apparently some of our Gen Z listeners didn't realize that was referring to the artist 50 cent. His song in the club was huge. It came out in 2003. why this song though? Like why not Beyonce or Outcast who also had hits that year? It's interesting that the artist she chose to mention has that connection to Money 50 cents. What could she be saying with that choice? One possibility is that it was a small price to pay to find out something so important, you know, connects to the word cheap in the previous verse, and it was not convenient. Would've been the best mistake, should have kissed you anyway. So she was worried it would've been a mistake. Why? Now she thinks it would've been a good mistake to make. It's an interesting question, this idea of a mistake being a good thing, like how could making a mistake be good? It reminds me of failure brings freedom from Opalite. It seems like she was worried that kissing him would have ruined the friendship, which she makes explicit at the end of the song, but now she thinks it would've been worth it. So even if she failed, meaning that it did mess up the friendship, or maybe he didn't feel the same way or something else negative happened, it would've been better to know. Then we come to the bridge. Don't make it awkward in second period. Might piss your ex off. Lately we've been good. Could this be him talking? It definitely seems to be reasons not to kiss him. And the fact that it says we've been good indicates this is something they actually talked about being good by not spending too much time together, by not flirting, not being alone together. Staying friends is safe. Doesn't mean you should. This sounds like her older self. Again, it might be safer to stay friends, but that doesn't mean it's the best choice. Verse three, when I left school, I lost track of you. Abigail called me with the bad news. Goodbye, and we'll never know why. On first. Listen, we're not quite sure yet why it's goodbye what the bad news is, but we're starting to suspect. We'll never know why has multiple meanings. Like never know why he died, never know why they fell out of touch. Never quite know why they never kissed. Then the chorus. It was not an invitation, but I flew home. Anyway, with so much left to say. So much left to say tells us it wasn't just about a physical kiss. It was about telling him how she really felt, probably that she loved him and now she can't. The closest she can come Is whispering it at his grave. Then the post chorus tells us the moral of the story, giving us the advice to ruin the friendship, to answer the question, rather than spending the rest of your life wondering. We've been talking a lot about dissonance on this album, and this song seems to lack that sense of being off balance within the music But in context of the larger narrative, it's incredibly dissonant. In the midst of her massive career success, she's suddenly thrown back into the world of high school, flooded with memories and full of regret. Suddenly, none of that showgirl life seems to matter, just this aching personal loss. There's also a subtle tension within the lyrics, some irony regarding the title. It's a directive to ruin the friendship, but it's really about seeking intimacy, about being vulnerable, even if that means risking the very relationship you want to protect. She's leaning into the vulnerability that was introduced in eldest daughter. To have kissed him would've been to make herself vulnerable. How would he respond? What would other people think? She didn't want to take that risk. She didn't want to be labeled the bad girl who made this guy cheat on his girlfriend while she was out of town, but now she's asking why was I so concerned about that? There are much worse things than having been rejected by that guy or having been talked badly about in high school. Now 10 or however many years later, that seems like a small price to pay in exchange for being fully honest with this person she cared so much about. She also seems to be longing for a quieter, more honest life, but only now that it's no longer within reach. It reminds me of the Elizabeth Taylor line where she says she trade the Cartier for someone to trust. Just kidding. would she really go back? Would she really trade this showgirl life to be with this guy from high school? It seems unlikely that this guy would bloom under the bright lights he would probably wilt, so the relationship most likely wouldn't have lasted just like the friendship didn't last, even though she never kissed him It was ruined anyway. Still, there's something powerful here about her longing for what could have been. It reminds us that no matter which path we take, there will always be others that we'll never get to explore. No matter how great our life is, we can always wonder if the grass might have been greener. No matter how much we achieve, there will always be someone we didn't kiss, a road, we didn't take a version of ourselves. We'll never meet. The showgirl can dazzle the world, but she can't undo the quiet heartbreak of wondering what might have been. This song reminds us as the experience reminds her, that beneath the costume, she's just as human as the rest of us, be regrets and self-doubt Only now she isn't sure what will remain when the spotlight fades. Will anyone still love her if she reveals she's just an ordinary woman? But this reflective space is short-lived. The next song finds her at war, leaning into sharpness and cruelty. The shift is jarring, almost violent, reminding us that there's no room for tenderness in the ruthless world of showbiz. Here are your discussion prompts for this lesson. I'd love to hear your thoughts in the comments. Number one, this track is tender and reflective while the next song actually romantic is sharp and confrontational. Why do you think Taylor placed them back to back on the album? How does this tonal contrast affect your understanding of the album's narrative arc? Number two, how does the theme of people pleasing intersect with the showgirl persona? In what ways does the song and the album as a whole explore the costs and consequences of extreme people pleasing? And now for your writing prompts. We'll start with memoir. Number one, pick a vivid memory from your adolescence or young adulthood that still lingers. Describe it with precise sensory details and reflect on how it shaped your understanding of yourself and others. Number two, what regrets have haunted you in your life? What paths not taken do you wonder about? Choose one and write about the alternate reality that might have been. You can engage your imagination here and write it almost like fiction based on what you think could have happened. And number three, in what ways do you play it safe in your life? Is there something you would do if you knew you wouldn't get in trouble, however you would define trouble What potential consequences keep you from taking that risk? And now for fiction, number one, write a story where you have the main character encountering a similar dilemma three times at different stages of life. Try to have the internal conflict intensify with each instance so that it builds and you get something new, a new perspective or layer with each successive scene. Number two, create a story about two characters who share an unspoken attraction, but never act on it. Use alternating perspectives to show their private thoughts and regrets over time. You could even do that with the story of this song. What do you think the guy she's singing about was thinking and wondering? You know, how did he feel when they didn't kiss? Why didn't he kiss her? How did he feel when she left and got famous? Could be an interesting exercise. And number three, if you have a work in progress, add a scene toward the middle where the mean character or the antagonist experiences a moment of tenderness that reveals something unexpected about them, something the reader hasn't seen yet that adds depth to their character. And if you haven't already, remember that you can sign up to receive these writing prompts in a document where you can access them easily in writing. Just go to mara er.com/prompts and enter your email address and they'll get sent to your inbox. And I wanna make sure you know that I have a workshop coming up called Write like Taylor Swift, where I'm gonna teach you how to use the most impactful strategies that make her songs so great in your own writing, whatever kind of writing that is, whether it's memoir or fiction or poetry. It's gonna be going down on December 10th, so mark your calendar and stay tuned for updates and the chance to register. It's gonna be a lot of fun. And that is it for today's lesson. As always, thank you so much for joining me here for this literary analysis And pop culture fun. if you're loving these deep dives. Make sure to follow the podcast or come join the discussion on social media. My links are in the show notes. I'd love to hear your questions, comments, and insights. class is always about bringing you into the conversation, helping you to do your own thinking and come to your own conclusions, so I'd love to see you involved. Until next time, class dismissed.