Tear Jerker / Taylor Swift

This country-pop singer can do some very emotional songs.
  • The monologue at the beginning of "I Knew You Were Trouble" can be this for anyone who has ever been in an abusive relationship.
    • The middle eight, too:
    And the saddest fear/Comes creeping in/That you never loved me/Or her, or anyone, or anything
  • This one is probably more of a Heartwarming Moment than anything, but the ending to the video for "Love Story" can get to certain people. Particularly when the couple being compared to good ol' dead Romeo and Juliet, having been split up by Juliet's dad, reunite, and the chorus is sung a bit differently...* sniff* It's better if you hear the whole song.
    "Marry me, Juliet, you'll never have to be alone
    I love you, and that's all I really know
    I talked to your dad, go pick out a white dress
    It's a love story, baby, just say yes..."
  • One can be deeply affected by "White Horse", with its quite frankly miserable lyrics about having overly high hopes for a relationship. Take a wild guess why.
    • The video is even more of a tearjerker, expounding on the storyline of a boyfriend who cheats on his girlfriend by dating another girl behind her back. A friend meets with the female protagonist (played by Swift) to break the news of her boyfriend's betrayal and arms her with information about what to look for. When she confirms her friend's information, she breaks up with him. She then goes home to cry her eyes out, the solemn scene punctuated by heavy rain outside note , before the boyfriend calls to give him another chance; she tells him no, hangs up on him and begins bawling her eyes out again.
  • "Innocent". Doubles as Heartwarming when you think of the song's context and who it's for.
  • "Never Grow Up" from Speak Now. It's all about the innocence of childhood gradually disappearing; Taylor tells the kid she's singing to "never grow up", and it's heartbreaking. She even sounds like she's crying at one point, too.
    So here I am in my new apartment
    In a big city, they just dropped me off
    It's so much colder than I ever thought it would be
    So I tuck myself in, turn my nightlight on
    Wish I'd never grown up
    Wish I'd never grown up
  • If you've recently broken up with a summer romance, or the one that got away broke up with you in the fall, "Tim Mc Graw" can reduce you to tears.
  • "Invisible" was a bonus track on Taylor's first album. Anyone who has ever been in unrequited love with someone who, in turn, was in unrequited love with someone else have their heart ripped out by this song.
    "We could be a beautiful, miracle, unbelievable/instead of just invisible
    Like shadows in a faded light/ Oh, we're invisible."
  • And "The Story of Us", although the music video implies that there's still hope.
  • "Dear John" in every sense of the word.
  • "You're Not Sorry". For anyone who's ever been betrayed by someone they loved.
  • The plainly spoken heartbreak of "If This Was a Movie" qualifies too. Who hasn't felt exactly like that before?
  • "Safe and Sound," especially when taken in the context of the movie it was written for (The Hunger Games). Listen to it and think of the scene with Rue and the flowers (you know the one), and say with a straight face that it doesn't make you at least WANT to cry.
    • Also with the music video, it almost feels like Taylor is playing the ghost of Prim Everdeen, seeing District 12 after the war.
  • Her cover of "Drops Of Jupiter" (Originally by Train) on her Speak Now Tour live CD is not for public listening, you will cry!
  • "Enchanted" will bring the emotions in a positive sense.
    and I was enchanted to meet you
    • The bridge, where Taylor begs the person she's singing to, "Please don't be in love with someone else. Please don't have somebody waiting on you..."
    • The song was written about Taylor meeting Adam Young, better known as Owl City, and her infatuation with him. Later, Adam released a cover of the song... singing directly to Taylor. It's hard not to tear up at the final line:
    I just wish you knew, Taylor, I was so in love with you.
  • "Haunted" to anyone who's had a tough time letting go.
    Come on, come on, don't leave me like this
  • Her charity single "Ronan," inspired by a blog created by the mother (credited as co-writer) of a four-year-old who died of cancer, is even more powerful when you learn Swift used only phrases from the blog -and therefore this is true insight into what it's like to lose someone so young. After the song's bridge Swift can be heard inhaling as if trying not to sob:
  • "Back To December", about regret over a relationship haunted by emotional baggage, and the sadness that the relationship may never heal, counts for one, too.
    • Even sadder in that, despite the public often accusing Taylor of never taking the blame for failed relationships this song is her desperately apologising for being cruel and utterly crushing the boy it's about. Also seemingly filled with ambiguous lines plucked straight from the last argument the two of them had.
      This is me swallowing my pride, saying I'm sorry for that night
  • "The Moment I Knew". after listening to that song, you would like to give Taylor a big hug.
  • "Red", to those who have intense love affairs which "ended so suddenly".
  • "All Too Well", where to start, the regret in this song is so strong you can taste it. It's a five and a half minute piano ballad filled to the brim with painstaking detail. This includes road trips, scarves left at houses, family photo albums, nights spent dancing in the light of the refrigerator and Taylor being paralyzed by time after the break up.
    You call me up again just to break me like a promise. So casually cruel in the name of being honest.
  • "Come Back...Be Here" to anybody who ever missed anyone ever.
  • "I Almost Do" to people who could almost make up with someone but for some reason can't.
  • "Sad Beautiful Tragic" "Words, how little they mean, when they're a little too late".
  • "Mean". For anyone who has ever been in an emotionally or physically abusive relationship, those lyrics can really trigger memories of rock bottom, and the need to pull yourself out.
    • As well as for anyone who has been bullied.
  • "Tied Together With A Smile" from her first album. It's written about a friend of hers who had bulimia, and a person who's losing it but is hiding behind a smile but still coming undone. The secret message is 'you are loved'. Could double as a Crowning Moment of Heartwarming
  • Not released on an album (yet), but "Brought Up That Way", an unreleased song from a father's point of view about watching his daughter grow up and nearly losing her, is about as heartbreaking as it can get.
    He says, "God, I didn't bring her up to watch them lay her down
    Nearly killed me the day they put her mama in the ground
    Only thing kept me alive was that little girl's smile
    So please, don't take that away
    It won't be easy taking her today
    She wasn't brought up that way."
  • Happy tears at the ending of the "Ours" music video, where Taylor reunites with her boyfriend after he's been deployed. It's a beautiful moment.
  • Teardrops on my Guitar can be this for anyone who has ever had to tell themselves "I Want My Beloved to Be Happy".
  • "Last Kiss"
    So I'll watch your life in pictures like I used to watch you sleep
    And I feel you forget me like I used to feel you breathe
    And I keep up with our old friends just to ask them how you are
    And I hope the sun shines
    And it's a beautiful day
    And something reminds you
    You wish you had stayed
    You can plan for a change in weather and time
    But I never planned on you changing your mind
  • "Blank Space" doesn't sound too sad until you realize she's singing about adding yet another guy to the list of ex-lovers who think she's insane.
  • "Forever and Always" (the piano version) is very tear jerking when you think about your failed past relationships.
  • "Clean," about finally moving on from a bad relationship. It's triumphant, but also very sad.
    Ten months sober, I must admit
    Just because you're clean don't mean you don't miss it
    Ten months older, I won't give in
    Now that I'm clean I'm never gonna risk it
  • The ending of the "Wildest Dreams" music video. Taylor's character finds out that her co-star, who she had an affair with while filming their movie, is married, and finally just leaving, ignoring him when he runs after her.
  • Joyful tears at "You Are In Love", which details the romance between one of her producers, Jack Antonoff and her friend Lena Dunham. It's one of the few slow songs on 1989 and only on the deluxe version, but boy is it worth it.
    One night, he wakes.
    Strange look on his face.
    Pauses, then says:
    You're my best friend.
    And you knew what it was.
    He is in love.
  • Despite being a dark song 'Look What You Made Me Do' has a couple. 2016 was a hard year for Taylor with public scrutiny surrounding her from all sides. Thanks to this the carefree kind girl everyone saw is gone, in her place is someone who's innocence has been crushed and now is unable to trust anyone around her and is angry as a result.
    "I don't trust nobody and nobody trusts me"
    "I'm sorry, the old Taylor can't come to the phone right now. Why? Oh, 'cause she's dead!"
    * "Delicate" is based on the assumption that love is too good to be true because Taylor can't believe anyone would stick with her given her recent issues in the media, and the music video is all about how she feels she can't be herself in the public eye.