10 Taylor Swift Songs I Love to Cry To

If you're going to let those teardrops fall, they may as well land on your guitar.

10 Taylor Swift Songs I Love to Cry To

Maybe I’m weird, but sometimes I just need to cry. The release of tears seems to get all the pent-up angst and sorrow out of my system as well. Sometimes I’m sad over something specific; sometimes I’m simply in a mood. Either way, there are moments (too many probably) where I just need to cry.

There are occasions, however, where I can’t seem to get the healing tears flowing. That’s when I turn to music. The majority of the time, that music tends to belong to Taylor Swift. Here’s a list of ten songs by Taylor Swift that you might want to listen to next time you need a good cry!

1. "Cold As You"

Taylor’s self-titled debut was an exceptionally emo album when you dig into the deep cuts. The original track 5, “Cold As You” features some of Swift’s most heartbreaking lyrics. It’s all about a guy who Taylor adores, but he is distant, uncaring, and, well, cold. The lyric that breaks my heart every time says, “You put up walls and paint them all a shade of grey / And I stood there loving you and wished them all away / And you come away with a great little story / of a mess of a dreamer with the nerve to adore you.” “Cold As You” is the story of a girl who gave every part of her heart to someone who gave her nothing but rejection and heartbreak in return. For being a young teen at the time this track was written, Taylor certainly felt this heartbreak deeply, writing in the song’s bridge, “You never did give a d*mn thing, honey, but I cried, cried for you / And I know you wouldn’t have told nobody if I died, died for you.” Ouch. “Teardrops On My Guitar” may be the more famous cry-along track on Taylor’s debut, but the brutally vulnerable writing of “Cold As You” makes it my go-to Fetus Taylor crying song.

2. "Breathe"

Taylor once said of this Fearless track, “It’s crazy listening to the song because you’d think it’d be about a relationship, but it’s really about losing a friend and having a fallout, just the loss.” I think “Breathe” is even more of a universal song than many of Taylor’s relationship songs. Not everyone has had a whirlwind romance or a devastating breakup, but almost everyone has lost a friend due to a fallout, losing touch, or some other circumstance. One lyric that particularly gets to me in “Breathe” is, “People are people and sometimes we change our minds / But it’s killing me to see you go after all this time.” Taylor admits the sad fact that sometimes people just change their minds, break their promises, and decide to leave. But that doesn’t make it hurt any less when they inevitably do. Lyrics like “I don’t know what to be without you around,” “You’re the only thing I know like the back of my hand,” and “I can’t breathe without you” tell the listener how close Taylor was with this person. Sometimes the fallout of a friendship can hurt just as much as—or even more than—a breakup with a boyfriend or girlfriend. The song (which features Colbie Caillat), end with a trailing lyric repeated in the background, “I’m sorry, I’m sorry, I’m sorry…” If you’re not crying at this point, you’re listening wrong.

3. "White Horse"

Ah, who doesn’t remember crying over their non-existent ex-boyfriend to this song after school in seventh grade? Watching Taylor sob bitterly on the floor in the music video is one of my most vivid memories from that era. In this track, Taylor realizes her relationship isn’t the fairytale romance she first thought it was. There will be no happily ever after, she’s no princess, and he’s certainly no prince. The first half of “White Horse” contains a lot of self-blame for why the relationship didn’t work out. She thinks, “Stupid girl, I should’ve know,” “I was naïve,” and “My mistake, I didn’t know to be in love / you had to fight to have the upper hand.” However, Taylor’s mindset changes later on. In the bridge, her former love comes to her, begging for forgiveness. With an apology of her own, Taylor declines to take him back. She’s realized that he never loved her the way he should have (“I’m gonna find someone someday / who might actually treat me well”). She will have so many more opportunities to find happiness in her life, so she’s riding off into the sunset on her own. The tagline of “White Horse” transitions from “It’s too late for you and your white horse / to come around” to “It’s too late for you and your white horse / to catch me now.” Rather than Taylor being left all alone, she is choosing to move on without him. Try and catch her now.

4. "You’re Not Sorry"

Wow, Fearless had a lot of stripped-down, tear-jerking songs on it. “You’re Not Sorry” details a relationship where Taylor has given this boy second, third, and fourth chances to the point of exhaustion. She was extremely dedicated to this relationship and by no means wants it to end (“Could’ve loved you all my life / if you hadn’t left me waiting in the cold”). However, she realizes this person she’s poured so much of her heart into isn’t sorry for all the times he’s let her down, and he’s never going to change. She sorrowfully tells him not to call anymore, because she won’t answer. She’s heard it all and, no matter how badly she wants to believe it, she just knows he isn’t truly sorry for all the lies, secrets, and heartache he’s caused her.

5. "Back To December"

So many sad songs seem to center around the month of December. Maybe it’s the cold weather. Maybe it’s the loneliness that comes from spending so much time indoors to escape the snow. Or maybe it’s that time you left the roses your boyfriend gave you to die in the winter air. That’s what it was for Taylor. In this Speak Now track, the tables have turned. This guy gave Taylor “all [his] love,” and she let him go. “Back To December” expresses the regret she feels after not realizing what she had until it was gone. This is the kind of regret that hangs over a person constantly, something you can't help reliving over and over (“I go back to December all the time,” “These days I haven’t been sleeping / Staying up, playing back myself leaving”). Taylor reaches the bridge with wishful thinking, hoping one day she’ll get the chance to make it right. But she admits that she understands what has occurred, and she still returns to December in her mind time after time.

6. "Last Kiss"

How dare you get me started on this one. On the back end of Speak Now, “Last Kiss” is an emotionally intense, melancholy ballad guaranteed to make you cry. The intro music itself is enough to evoke strong emotions in anyone. “Last Kiss” is about a breakup Taylor never saw coming—she never imagined they’d share a kiss for the very last time. Taylor goes through each verse of this song by detailing the little things she remembers about this relationship. Those small, intimate moments in a relationship tend to be the most painful memories to recall when it’s over. From the look on his face in the darkness, the scent after the rain as they reunited, the way he walked…she remembers all of it in painfully vivid detail. She holds on to those memories just as she holds on to pictures of him, keeping tabs on him through mutual friends, hoping that one day he’ll miss her and wish he could go back to what they had.

7. "All Too Well"

Our first track on this list from Red, “All Too Well” is overwhelmingly the fandom’s favorite track 5. “All Too Well” is reminiscent of “Last Kiss,” featuring Taylor reminiscing on the intimate details of a past relationship. She remembers everything so well, so clearly. Something “All Too Well” does differently from “Last Kiss,” however, is that it goes into stronger detail about the pain and sadness Taylor felt when the relationship ended, as well as the impact it has on her to this day. After a building, intense description of the pain she endured, the song slows down and Taylor softly sings, “Time won’t fly, it’s like I’m paralyzed by it / I’d like to be my old self again, but I’m still trying to find it.” She earlier describes this relationship as a “masterpiece” before her partner ruined it. This relationship, both the good and the bad of it, changed Taylor. She was a new person because of it. As she says in the opening monologue of the “I Knew You Were Trouble” music video, “I think that the worst part of it all wasn’t losing him, it was losing me.” Truly heartbreaking.

8. "I Almost Do"

Red is known for being the most emotionally diverse of Taylor’s albums. While your favorite sad song may be from another of her albums, there is no doubt that Red has the most sad songs of any Taylor Swift record. “I Almost Do” paints a picture of Taylor sitting around one evening, making bets on what her former beau is doing at that very moment. This is someone she knows deeply. She often thinks of calling him up or running back into his arms, but every time she’s about to do so, something stops her. A clue to what that something might be comes in the song’s second verse, in which Taylor sings, “I bet it never, ever occurred to you / That I can’t say hello to you and risk another goodbye.” She desperately wants to reach out to him. He has made attempts to reach out to her, but she never replies for fear of another heartbreak. She tells him through this song that it’s probably better for both of them this way. But no matter how true that is, she can’t stop herself from wanting to “try again” with him. And every time she doesn’t, she almost does.

9. "Sad Beautiful Tragic"

“Sad Beautiful Tragic” is the song I believe I’ve cried to the most. Partially that is due to personal experience, but this track is exceptionally sad lyrically and structurally. Taylor’s vocals are soft and haunting on this song. The first verse reveals that her former love tried to make things right at some point, but that his attempt to fix her broken heart was made too late to truly mean anything (“Words, how little they mean when you’re a little too late”). Taylor adds a note of personal disappointment here when she sings. “Good girls, hopeful they’ll be and long they will wait.” She has longed for a magical love for so long, yet every time she is disappointed. The song goes on to describe their “love affair” as magical and beautiful, yet tragic and sad. She still dreams of him at night, then feels the literal and emotional distance between them when she wakes in the morning. Time, she says, is “taking its sweet time erasing” him. The structure of the chorus and bridge of “Sad Beautiful Tragic” is somewhat choppy and less fleshed-out than the verses. This is purposeful. It evokes a certain melancholy in the listener. Taylor once described this favorite of mine as, “a cloudy recollection” of this relationship, stating the overall emotion she felt at the time of its writing as “wistful loss.”

10. "The Moment I Knew"

One of Taylor’s saddest tracks to date, “The Moment I Knew” tells a true story in crushing detail. This Red bonus track is the account of Taylor’s 21st birthday, where her boyfriend, who promised to be there, didn’t show up. She once said in an interview that the day she sings about in this song was “the worst experience ever.” She imagines how this scenario could have been different, how he could have simply kept his word, shown up, and made her the happiest girl in the world. But he didn’t. And because of that, she spent her 21st birthday holding back tears in front of everyone and crying in the bathroom. She says it all occurred in “slow motion,” looking around the room, seeing everyone she loved in the same room for her special day… everyone except the person who was the most special to her. And if the heart-wrenching lyrics and the overall sorrowful sound of the song aren’t enough to make you cry, just imagine yourself at your 21st birthday, waiting patiently for your boyfriend to show up and absolutely make your day, only to realize he was never planning on coming. What kind of evil person was this man??? Fans know, but that’s a discussion for another day.

Thank you so much for reading! I’ve been absent here for quite a while, but please let me know if you’d like more of these kinds of articles or what you’d like me to write about next! You can catch me on Twitter @LilyKristian.

song reviews
Lily Kristian
Lily Kristian
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Lily Kristian

Future broadcast journalist and lifelong Swiftie!

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