An earlier version of his article was originally published here when I wrote for the Odyssey Online.
Taylor Swift has had a song for every boy problem you’ve had since you were 13 and Joey stood you up for the 8th-grade dance. Whether you love her or hate her, Miss 1989 has a knack for taking heartbreak and nailing it with each passive-aggressive lyric. Yes, she writes songs about other things, but this is what initially made her famous. If you say you’ve never locked yourself in your room, cranked up some T-Swift, and cried, you’re a filthy liar. Having had more extensive knowledge in this matter than I care to admit, here’s a careful analysis of what some of Taylor’s best breakup anthems reveal about your love life.
1. “Dear John” (Speak Now, 2010)
This guy screwed you over, big time. Dripping equally with venom and unapologetic pain, I always wondered what exactly John Mayer did to deserve getting torn to absolute shreds in this six-minute, soul-destroying ballad. One of my all-time favorites.
“I should’ve knooown…”
2. “Forever And Always” (Fearless, 2008)
Looking at you, Joe Jonas. This song single-handedly helped me survive the majority of my high school heartbreaks. Is there anything worse than watching everything fall apart, and feeling powerless to stop it?
“You stare at the phone, he still hasn’t called, and then you feel so low you can’t feel nothing at all, and you flash back to when we said forever and always…”
3. “I Knew You Were Trouble” (Red, 2012)
Honestly, are you even surprised? A scenario I’m all too familiar with: a boy with a bit of a reputation shows interest in you, you know better but go for it anyway… and he turns out to be exactly the manipulative douche everyone says he is.
“Cause I knew you were trouble when you walked in…”
4. “We Are Never Ever Getting Back Together” (Red, 2012)
The title says it all. You’ve finally realized that your on-again, off-again relationship isn’t worth your time.
Sing it with me now: “Cause weeeeeee are NEVER EVER EVER EVER, getting back TOGETHER!”
5. “The Last Time” feat. Gary Lightbody (Red, 2012)
One of T-Swift’s seldom-known, most incredibly underrated songs, it almost plays out as the flip side to the previous song on this list. A tragic duet about two lovers, who’ve evidently come in and out of each other’s lives many times, finally admitting that this is the end.
“This is the last time I’m asking you this, put my name at the top of your list…”
6. “The Story of Us” (Speak Now, 2010)
Another personal favorite. You know that first time you spot your ex in public after you break up? And you have to pretend you don’t see each other but you both totally DO and it’s so awkward that you want to crawl under the table and die? This song is for you, my friend.
“Now I’m standing alone in a crowded room and we’re not speakin’, and I’m dying to know, is it killing you like it’s killing me?”
7. “All You Had To Do Was Stay” (1989, 2014)
You’ve been over for a while, and now he’s trying to come back into your life. Blast this one to prevent yourself from responding to his texts. You had your shot, Harry Styles.
“Here you are now, calling me up, but I don’t know what to say. I’m still picking up the pieces of the mess you made…”
9. “All Too Well” (Red, 2012)
You’re probably on your second box of cookies and/or laying on the floor. Jake Gyllenhaal, what’s good?
“You called me up again just to break me like a promise, so casually cruel in the name of being honest…”
10. “Cold As You” (Taylor Swift, 2006)
One of the saddest in her discography, this song brings back every devastating feeling of rejection you’ve ever had. It’s the very essence of the moment when you realized your crush would never like you back set to a melody. One of Taylor’s few songs that denotes utter defeat, there is no backlash, no barbed remarks; just raw misery. It’s the feeling that you’re never going to be good enough for somebody; it’s sobbing into your pillow; it’s knowing you gave your all and they gave you nothing; it’s feeling like an idiot for thinking you ever had a chance.
“And you come away with a great little story, of a mess of a dreamer with the nerve to adore you…”
11. “Last Kiss” (Speak Now, 2010)
Another slow, sad lament, though apparently a semi-apology for “Forever and Always.” Perfect for collapsing on the floor, crying hysterically. Joe Jonas, why?
“Never thought we’d have a last kiss…”
12. “Picture To Burn” (Taylor Swift, 2006)
The one that started it all, this was Taylor’s original “bad breakup” anthem that paved the way for other such hits. It’s childish, hilariously petty, and brilliant. You probably blasted this one and sang along with your best friend after your boyfriend of 3 weeks dumped you after Algebra.
“I hate that STUPID OLD PICKUP TRUCK YOU NEVER LET ME DRIVE, YOU’RE A REDNECK HEARTBREAK WHO’S REALLY BAD AT LYING…”
13. “Clean” (1989, 2014)
Is there any greater relief than the moment that you realize you’re finally 110% over someone?
“I think I am finally clean.”
14. “Back To December” (Speak Now, 2010)
Maybe you’re the one who made a mistake, and didn’t know what you had lost until it was too late. Sorry, Taylor Lautner.
“So this is me swallowing my pride standin’ in front of you saying I’m sorry for that night…”
15. “Fifteen” (Fearless, 2008)
Says it all about your first love, being young and naive, and those first lessons you learned.
“Cause when you’re FIFTEEN, and somebody tells you they love you, you’re gonna believe them…”
16. “The Way I Loved You” (Fearless, 2008)
You’ve supposedly moved on and know you should be happy, but you can’t get him out of your mind no matter how hard you try.
“I miss screamin’ and fightin’ and kissin’ in the rain, it’s 2am and I’m cursing your name, we were so in love that we acted insane and that’s the way I loved you…”
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