Welcome or welcome back to Analysis of a Song, the series where I pick a song and break down the lyrics section by section. I thought it high time we looked at another Taylor Swift song. Last time, I analysed what I think is one of her saddest songs — So Long, London. This time, we’re looking at another one of Taylor’s saddest songs. Dear John. This is one of my stan songs. It’s my favourite song from Speak Now and my second favourite Taylor song overall. I am of the unpopular belief that this song is better written and more devestating than All Too Well (the five minute version).
I have never in my life experienced anything even remotely similar to what Taylor is describing in this song. And yet, every time I listen to it, I feel it so deeply. I feel as though I have experienced what she is describing. And that, my friends, is the power of great songwriting. Without further ado, let’s get into the lyrics.
Verse 1
Long were the nights when my days once revolved around you
Counting my footsteps, praying the floor won’t fall through again
And my mother accused me of losing my mind
But I swore I was fine
It’s no secret this song is about a relationship Taylor was in with a man who was significantly older than her. More specifically, she was 19, and he was 32, so there was a 12 year age gap. That is important context to know when understanding this song. She’s setting the scene in the opening lines. This person was everything to her. They were her world, to the point where her days revolved around them. I’m reminded of a line from august: “I cancelled my plans just in case you’d call. Back when I was living for the hope of it all.” I’m also reminded of a line from Superman, a song that is rumoured to be about the same guy Dear John is about: “Wishing the flowers were from you. Wishing the card was from you. Wishing the call was from you.”
Taylor is so infactuated with this person that she is willing to sit around all day, just in case they might happen to call or text or want to make plans. She carves out her day based around him. But then the night hits. Anyone who knows anything about Taylor’s discography knows nighttime is a huge motif in her works (she even has an entire album called Midnights). If someone is up by themselves late at night, chances are they’re pacing the room while ruminating in their thoughts and being consumed with anxiety and worry (something we know Taylor loves to do).



She would spend the day with this person, having them fill up her every thought, and then when her head hit the pillow that night, the anxiety would creep in. I’m sure we’ve all heard the saying: the body keeps the score. When we spend time with someone who is bad for us, even if we haven’t realised it yet, the body will reflect it. You know when you spend time with a toxic person, how afterwards you feel really low? Like they’ve brought down your energy and spirit?
A key theme of this song is manipulation. The person Taylor is describing in the lyrics is someone who is highly manipulative; someone who likes to play mind games. This includes gaslighting. Gaslighting is a manipulation tactic used to make someone question themselves and their own sanity, and that is definitely evidenced in the next line: “Counting my footsteps, praying the floor won’t fall through again.” You get this image of Taylor pacing her room late at night, counting her footsteps as she walks, feeling as if she’s going crazy and desperatley hoping this person won’t do anything else to completely derail her again.
The next line again adds to this idea. Her mother can tell something is wrong. She’s noticed the change in Taylor, so she’s concerned. But Taylor will just keep insisting everything is fine, even though her mother sees right through that lie. But she’s not only trying to convince her mother everything is fine, she’s trying to convince herself. She wants to be with this person, so she’s burying her head in the sand and ignoring all the obvious red flags. But deep down, she knows everything is not fine.
Verse 1 (part 2)
You paint me a blue sky
Then go back and turn it to rain
And I lived in your chess game
But you changed the rules every day
Wondering which version of you I might get on the phone tonight
Well, I stopped picking up and this song is to let you know why
Again, she’s really emphasising how manipulative this person was. One moment, they’d be so warm and loving and caring; they’d paint her skies blue and woo her with romantics. And then the next moment, with no warning whatsoever, they’d be cold and distant and cruel; those same skies would now be pouring down with rain. I can’t imagine how exhausting it must be dealing with a person like that; how much it would wear you down mentally. They can’t be cold all the time, otherwise you’d run for the hills, so they show you just enough love to always keep you staying.
Manipulative people are often hard to decode. You never know when they’re being genuine; you never know if they’re being sincere or if they’re just messing with you. They’re like a riddle that is impossible to solve. To them, everything is a game, with winners and losers. When Taylor was with this person, she felt like she was living in their little game, except it was impossible for her to win, because they would change the rules of the game constantly. She couldn’t win. No matter what she did, she would always lose.
She reiterates again how hot and cold this person was. She would be apprehensive every night before he’d call because she’d never know which version of him she was going to face: was she going to get the version of him that was warm and caring, or the version of him that was cold and distant? Or would she get one of the other varying, confusing versions of him? Every time they’d talk, it would be like talking to a completely different person. She could never make sense of him. She could never decode him.
The last line of the verse is her letting both him and the audience know she’s finally had enough. She is not going to subject herself to these mental gymnastics any longer. She’s done with the manipulation, and the gaslighting, and the mind games. She’s reached her breaking point. She no longer has to worry about which version of him she’s going to get on the phone, because she’s not picking up the phone anymore. And if he wants to know why she stopped picking up… Well, the answer is in this song.
Chorus 1
Dear John,
I see it all now that you’re gone
Don’t you think I was too young to be messed with?
The girl in the dress cried the whole way home
I should’ve known…
Hindsight is 20/20. Now that it’s all said and done, Taylor realises how much he played her for a fool. “Dear John” may sound really obvious and direct considering who the song is about, but it has a clever double meaning. A “Dear John” letter is a letter written by a woman to their lover letting them know their relationship is over. The term was popularised in WWII, when many soldiers off fighting would get letters from their partner back home letting them know they’d found someone else. This is what Taylor is doing. She is writing this person a letter in the form of a song to let them know their relationship is over, and this is why.

For the first time, she brings up her age. She scolds him for messing with her when she was so much younger than him. The next line, “the girl in the dress cried the whole way home,” really emphasises how young she was. She doesn’t refer to herself as a woman, she refers to herself as a girl. She was just a girl. He was a man, and she was the girl he sent home crying back to her parents. “Girl in the dress” symbolises her innocence.
Even after scolding him, the chorus still ends with, “I should’ve known.” She blames herself. All the signs were right there, and she ignored them. Everyone warned her he was bad news, and she didn’t listen. She was so willfully ignorant that she can’t help but partially blame herself. Throughout the entire song, you can feel how angry and disappointed Taylor is with herself. She thought she was smarter than that. He showed her she wasn’t as clever as she thought she was.
Verse 2
Well maybe it’s me and my blind optimism to blame
Or maybe it’s you and your sick need to give love then take it away
And you’ll add my name to your long list of traitors who don’t understand
And I’ll look back and regret how I ignored when they said, “run as fast as you can”
When listening to Taylor’s earlier music, it’s apparent that when she was younger, she tended to see the best in people. She was an optimist, even to her own detriment. When Taylor met John, even though everyone around her warned her against him, she was determined to ignore the rough sides of him, and focus only on the good in him. Because that was simply the kind of person she was. He took advantage of that; he took advanatge of her naivety. He saw this young girl full of innocence and optimism and messed with her simply because he knew he could. And again, it is only in hindsight Taylor realises how foolish she was; how foolish she was for trusting this person and welcoming them with open arms, when she should’ve had her guard up. She’s again blaming herself.
But then she redirects her anger and turns it back on him. Maybe it’s not her optimism to blame, maybe it’s his sick and twisted need to mess with people; to shower them with love and then just as easily take it away. I’m reminded of a lyric from Would’ve, Could’ve, Should’ve: “Lord, you made me feel important, and then you tried to erase us.” One minute, he would show her so much attention and affection like she was his entire world, and then the next minute, it was like she didn’t even exist, like he didn’t care about her at all. She’s again reiterating how hot and cold he was; how he could switch at the drop of a pin.
The next line, “you’ll add my name to your long list of traitors who don’t understand,” is a common thing with toxic, manipulative people. They always have a long list of ex-friends and ex-lovers who cut them out, and somehow, it’s never their fault. They never see the pattern of them being the problem every time, the other person is always the problem. They don’t understand that it’s not normal to have so many people decide they don’t want to be around you anymore. Will this trigger any inward reflection? Of course not. Taylor knows she will just become another name on this person’s list. He will insist she was the problem. She just didn’t understand him, and that’s her own fault.
Taylor regrets not listening to the people who warned her. She thought all these people just didn’t know John the way she did. They hadn’t seen the soft side of him. She had. Sure, he had made some mistakes in the past, but haven’t we all? These were the excuses she told herself. The Speak Now deluxe track Ours is an interesting song, because it was written by Taylor when she was still blinded by her love for this person. She scoffs at the people warning her, saying: “Seems like there’s always someone who disapproves, they’ll judge it like they know about me and you (…) don’t you worry your pretty little mind, people throw rocks at things that shine.”

She even acknowledges John’s spotty past and brushes it off; “Ghosts from your past gonna jump out at me, lurking in the shadows with their lip gloss smiles, but I don’t care, ‘cause right now you’re mine.” She also speaks of John’s manipulative nature in an endearing light; “I love the riddles that you speak.” It’s funny how everything can seem so clear and obvious only in hindsight.
Chorus 2
Dear John,
I see it all now that you’re gone
Don’t you think I was too young to be messed with?
The girl in the dress cried the whole way home
Dear John,
I see it all now, it was wrong
Don’t you think 19’s too young to be played by your dark, twisted games when I loved you so?
I should’ve known
In Ours, Taylor says: “It’s not theirs to speculate if it’s wrong, and your hands are tough but they are where my belong in.” But now, she’s saying: “I see it all now, it was wrong.” She’s realised they were right all along. It wasn’t right for a 32 year old man to date a 19 year old girl. Instead of just saying she was too young, she specifically says she was 19. She wants to really drive home and emphasise how young she was. She was still a teenager, she wasn’t even in her 20s yet. She realises now that he never actually cared about her, he just wanted someone to be a pawn in his game. She genuinely loved him, and all he ever did was mess with her.
Taylor was a different person after this. There is who she was before this person came into her life, and there is who she was afterwards. Emotional abuse is often overlooked and underestimated, but make no mistake, it can leave a huge psychological impact on a person. Especially if your brain is still developing, as it was during this time.
Bridge
You are an expert at sorry, and keeping lines blurry
Never impressed by me acing your tests
All the girls that you’ve run dry have tired, lifeless eyes
’Cause you burned them out
But I took your matches before fire could catch me
So don’t look now
I’m shining like firewords over your sad empty town
Every time Taylor would vent her frustrations and feelings to John, he’d apologise, and he was good at making it seem like he was genuinely sorry, but he never actually meant it. In the beginning, Taylor would buy it. She would believe he was genuinely sorry which is why she’d keep giving him more chances. But she sees now he was just playing with her. He was also good at keeping the lines blurry; he would never be direct with her about what they were to each other or how he really felt about her. Taylor was never totally sure where she stood with him.
As has already been estabolished, John liked to play mental games with people. Even when Taylor would pass every test and be a step ahead, John would never be impressed. As Taylor said earlier, it was a chess game, but he changed the rules every day. She could never win with him. This person Taylor is referring to has a bit of a repuation when it comes to their dating life. Taylor has seen what happened to the other women who have dated him. He drained the life out of them; he killed their spark. Taylor was headed towards the same fate. He almost had her. But she stole his matches before he could burn her. She escaped.
One of the most powerful lines of the song is, “I’m shining like fireworks over your sad empty town.” Taylor sees it now, clear as day: she will go on. She will go on to thrive, she will continue to achieve so much in her career, and John… he will remain a pathetic little man who got a power trip out of messing with a 19-year-old girl.



Chrous/Outro
Dear John,
I see it all now that you’re gone
Don’t you think I was too young to be messed with?
The girl in the dress cried the whole way home
I see it all now that you’re gone
Don’t you think I was too young to be messed with?
The girl in the dress wrote you a song
You should’ve known
Don’t you think I was too young?
You should’ve known…
In the final moments of the song, Taylor changes the line, “I should’ve known,” to “You should’ve known.” No longer is she blaming herself. The girl in the dress he sent home crying has written him a song. He should’ve known that if he was going to mess with her, she wouldn’t hold back. He should’ve known she would write the most scathing song she could exposing him as the manipulative asshole he is. And with that, she gets the last word.
With this song, she’s reclaiming the power he took from her.
I will forever believe this is one of the most heart-wrenching songs on Taylor’s entire discography. But it’s also one of the most well-written. If you’ve enjoyed this, make sure to look out for my upcoming analysis of Dear John’s sister song, Would’ve, Could’ve, Should’ve.
See you in the next analysis,
Lilly :)
Omg i’ve saved it cause i can’t read atm but even that title alone just made me so excited!!! ✨