History TearJerker / TaylorSwift

* 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.

** Notice that NiceGuy isn't on ''one'' knee, as if he's proposing. The narrator already turned him down, and now he's on his knees begging her to reconsider.

'til someone's on their knees and asks you\\

* ''Music/{{Taylor Swift|2006}}'' (2006)

* ''The Taylor Swift Holiday Collection'' (EP) (2007)
* ''Beautiful Eyes'' (EP) (2008)

* ''Music/{{Fearless}}'' (2008)

* ''Music/SpeakNow'' (2010)

* ''Music/{{Red|2012}}'' (2012)

* ''Music/NineteenEightyNine'' (2014)

* ''Music/{{reputation}}'' (2017)

* ''Music/{{Lover}}'' (2019)

* ''Music/{{folklore|2020}}'' (2020)

* ''Music/{{evermore|2020}}'' (2020)

* 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

* 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."

* "[[https://www.youtube.com/watch?v=BabmBHVfSW0 You're Not Sorry]]". For anyone who's ever been betrayed by someone they loved.

* "Safe and Sound," especially when taken in the context of the movie it was written for (''Film/TheHungerGames''). 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!

* 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:
--> [[TalkingToTheDead What if I'm standing in your closet, trying to talk to you?]]
--> [[TragicKeepsake What if I kept the hand-me-downs you won't grow into?]]
--> [[HopeSpot What if I really thought some miracle would see us though?]]
--> [[OutlivingOnesOffspring What if that miracle was even getting one moment with you?]]

* "The Moment I Knew". after listening to that song, [[TheWoobie 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 [[UnusualEuphemism break me like a promise.]] So casually cruel in the name of being honest.
** The entire bridge is soulcrushing. Most of the song is sung softly and gently, but Taylor practically ''screams'' out the above line. It really does sound like she's about to cry...
** The last verse, describing how, inevitably, life must go on.
-->''Now you mail back my things, and I walk home alone.''
* "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".

* "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 SugarWiki/{{Heartwarming Moment|s}}.
* 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."''

* ''Teardrops on my Guitar'' can be this for anyone who has ever had to tell themselves "IWantMyBelovedToBeHappy".

* "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.

----

** The song somehow managed to be [[UpToEleven more heartbreaking and sad]] when Swift performed it live (something she said when the song released that she can't see herself doing for the forseeable future) during the ''Together at Home'' fundraising concert because now it applies to all the family of the Covid 19 patients.

* "marjorie" is already an incredibly bittersweet and sad song about [[GriefSong keeping someone's memory alive in your head despite them being gone]] (in this case, Taylor's own grandmother [[https://en.wikipedia.org/wiki/Marjorie_Finlay Marjorie Finley]]), but the bridge of the song verge ''hard'' into this territory as it captures, as Rolling Stone writer Claire Shaffer wrote, "the delayed tragedy of losing a loved one [[HeroOfAnotherStory when you're too young to see their full worth]]":

* "marjorie" is already an incredibly bittersweet and sad song about [[GriefSong keeping someone's memory alive in your head despite them being gone]] (in this case, Taylor's own grandmother [[https://en.wikipedia.org/wiki/Marjorie_Finlay Marjorie Finley]]), but the bridge of the song verge ''hard'' into this territory as it captures, as Rolling Stone writer Claire Shaffer wrote, "the delayed tragedy of losing a loved one when you're too young to see their full worth":

* "tolerate it" is an incredibly painful song about being in love with someone who doesn't appreciate you. The narrator is implied to be much younger and less experienced than her love interest and is drawn in by their maturity, but soon that maturity revealed them to be cold and unfaithful despite all of her best effort. At the end of the song she is implied to have a freak out and wanting to leave, but is implied that she can't yet. Some people even interpret the song is about a parental relationship, which made it doubly painful since the narrator is very likely a minor and literally can't leave on their own.

* "evermore", the closing track of the album of the same name, is about a narrator who is implied to have a DarkAndTroubledPast whose mind keep take her back to that darkest moment. Luckily, the memory of her lover brought her out of her darkness and she acknowledge that she can begins healing.

* "evermore", the closing track of the album of the same name, is about a narrator who is implied to have a DarkAndTroublePast whose mind keep take her back to that darkest moment. Luckily, the memory of her lover brought her out of her darkness and she acknowledge that she can begins healing.

-->''You'll get better soon, 'cause'' you have to''.''

-->''Don't call me "kid."''\\
''Don't call me "baby."''\\
''Look at this idiotic fool you've made me.''\\
''You taught me a secret language''\\
''I can't speak with anyone else.''\\
''And you know damn well''\\
''for you, I would ruin myself''\\
''a million little times.''
* "seven," in which the narrator describes a childhood friend who's heavily implied to be suffering from AbusiveParents.
-->''And I've been meaning to tell you,''\\
''I think your house is haunted.''\\
''Your dad is always mad, [[ChildrenAreInnocent and that must be why]].''\\
''And I think you should come live with me''\\
''and we can be pirates.''\\
''Then you won't have to cry''\\
''or hide in the closet...''

-->''The doctor had told him to settle down.''\\
''It must've been'' her ''fault his heart gave out.''\\
''And they said, "There goes the last great American dynasty.''\\
''Who knows, if she never showed up, what could've been?''\\
''There goes the maddest woman this town has ever seen.''\\
''She had a marvelous time ruining everything."''

''You taught me a secret language''\

* 2019's The Archer if you've ever suffered from anxiety...

-->"[[spoiler:Marry me, Juliet, you'll never have to be alone]]\\
[[spoiler:I love you, and that's all I really know]]\\
[[spoiler:I talked to your dad, go pick out a white dress]]\\

** Also with the music video, it almost feels like Taylor is playing [[spoiler: the ghost of Prim Everdeen, seeing District 12 after the war]].

* ''Happy'' tears at the ending of the "Ours" music video, [[spoiler:where Taylor reunites with her boyfriend after he's been deployed.]] It's a beautiful moment.

* The ending of the "Wildest Dreams" music video. [[spoiler: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.]]

--> "I'm sorry, the old Taylor can't come to the phone right now. Why? Oh, [[spoiler:'cause she's dead!"]]

--> "I'm sorry, the old Taylor can't come to the phone right now. Why? Oh, [[spoiler:'cause she's dead!"]]\\

* This one is probably more of a HeartwarmingMoment than anything, but the ending to the [[https://www.youtube.com/watch?v=NxdrgYy_SE8 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.

* "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 CrowningMomentOfHeartwarming

''[[CrowningMomentOfHeartwarming You're my best friend.]]''\\