70 Songs About Mistakes

Mistakes Are the Byproduct of an Active Life

Mistakes are the byproduct of a full, productive, and successful life. Don't fear them or beat yourself up over them. If you take any risks at all in your life, then you're going to make blunders, slipups, missteps, and errors in judgments both large and small. They happen to everyone. Learn from the experience without getting stuck but also:

"You must learn from the mistakes of others. You can't possibly live long enough to make them all yourself." – Sam Levenson, American filmmaker and actor

Some mistakes are embarrassing or even funny if they aren't happening to you—like that trail of toilet paper stuck to one's shoe or Freudian slips while public speaking. Others can have lifelong consequences—such as marrying the wrong person, having unprotected sex, or driving drunk.

Missing the winning shot in the championship game or hiring an employee who gets convicted of a corporate crime can certainly garner oneself high profile unwanted attention. Mistakes in interpersonal communication can also impact how others evaluate you. For example, if you happen to dangle a modifier or use the wrong its/it's or your/you're, then a grammarian will certainly notice.

The good news is that most mistakes are not actually the end of the world. Celebrate mistakes in love and life with a playlist of pop, rock, country, and R&B songs about mistakes, regrets, and learning.

1. "When I Was Your Man" by Bruno Mars

It was only after their breakup that the guy in this soulful 2013 pop ballad has come to realize how he had neglected the needs of his former partner. Looking back, he appreciates that he made a mistake by not investing in their relationship only now that she has found someone new who gives her the attention and affection that she never received from him. Filled with sorrow, the narrator can only hope that his former sweetheart is happy.

2. "Dawns" by Zach Bryan (Featuring Maggie Rogers)

The guy in this 2023 country crossover chart-topper stands on the front porch, unsure of why he and his estranged lover are even fighting. Their love has flamed out, and he wants his records and clothes back. He angrily declares their relationship a waste of his time.

The male narrator in this duet perceives love to be just another powerful drug with addictive effects, whereas the female narrator yearns for carefree days of going out to bars. When a romantic relationship breaks down and you've had it up to here with your partner, the desire to escape and move on is understandable.

3. "How to Save a Life" by The Fray

The protagonist in this plaintive 2005 alt-rock song recalls his last interaction with a troubled friend who had been battling fear, self-loathing, and thoughts of self-harm. Unable to save his friend, the guy makes the mistake of carrying his buddy's psychological burdens.

Where did I go wrong? I lost a friend
Somewhere along in the bitterness
And I would have stayed up with you all night
Had I known how to save a life

He blames himself for not doing enough to save his friend. In truth, however, the narrator didn't have the skilled training to save a life, Even then, it may not have been enough. Seek emergency professional help in such situations.

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4. "Beautiful Mistakes" by Maroon 5 (Featuring Megan Thee Stallion)

Two very different perspectives emerge regarding a couple's broken relationship in this 2021 pop single with a hip hop vibe. The man is depressed and spends a lot of time moping, lost in a fantasy world of the past. Wishing he had his honey back in his life, the guy tries to convince himself that she will return.

His big mistake was lying and breaking promises to his former girlfriend. His transgressions embarrassed her, and she is angry about his betrayals, particularly because he tried to behave like he didn't need her. Although his former significant other is out clubbing and enjoying her newfound single status, she still leaves the door open for reconciliation if he plays it right.

5. "If I Could Turn Back Time" by Cher

The woman in this 1989 rock track completely owns how wrong she was for what she said and did to hurt her lover and make him leave. The narrator acknowledges that "words are like weapons, they wound sometimes." Wiser now, she sincerely regrets the misdeeds that emotionally damaged her lover and chased him away. She cannot explain her behavior and wishes she could turn back time so that she could undo her mistakes.

6. "Mistake" by NF

You are more than your mistakes. In this mellow, searching pop ballad from 2023, a man is at crossroads in his life. Feeling that he's at a standstill, he looks for validation outside of himself. However, then he makes an important shift and justifies that while he may have made errors in judgment in his life, he himself is not a mistake. He may have qualities that need work and may have done things he's not especially proud of—haven't we all?—but he is deserving of love, understanding, and respect.

7. "New Person, Same Old Mistakes" by Tame Impala

When you embark on something new, whether it's a work project or a love affair, there's always the possibility of repeating the same old mistakes again. After all, we are creatures of habit. According to this 2015 psychedelic pop ditty, you have to take risks and face your fears even if there's a possibility of failure or regret. Mistakes help you grow and learn for the future.

8. "Be My Mistake" by The 1975

In trying to navigate young adulthood, the guy in this 2018 indie rock number searches for connection and love in the wrong place. As a result, he experiences regret and guilt. Feeling the emptiness of a casual relationship reminds him of the sweetheart he misses. The protagonist is trying to figure out what he wants and what kind of person he wants to be, and this isn't it.

9. "There Goes My Life" by Kenny Chesney

Sometimes what seems like a false step works itself out after all. In this 2003 country release, the narrator takes the listener back many years to when he was confronted with his partner's unwanted pregnancy. As a teenager, the narrator expresses that unwanted pregnancy threatens to ruin his entire life. "There goes my life," he remorsefully conveys. He sees his future disappear before him, thinking about this careless mistake.

As time passes, however, love for his daughter consumes the narrator. She grows from toddler to a young adult who leaves home, and the term "there goes my life" acquires a new and different meaning.

10. "Vampire" by Olivia Rodrigo

In this 2023 piano-driven hit, a young woman provides a scathing takedown of an ex-boyfriend. She claims that loving him was her biggest mistake— "six months of torture". The narrator also beats herself up for falling for his manipulative games and for ignoring other girls' warnings that he was bad news.

The lothario has a pattern of preying on girls younger than him. In retrospect, she can see that the player lovebombed her and made her appear unusually naive. This malignant man destroyed her trust, emotionally exploited her, and bled her dry. Now she is trying to recover from

The way you sold me for parts
As you sunk your teeth into me, oh
Bloodsucker, famef*cker
Bleedin' me dry, like a goddamn vampire.

11. "Call Out My Name" by The Weeknd

The pain of unrequited love hits hard for the guy in this 2018 R&B number. The protagonist describes becoming close and providing much needed support and comfort to a friend who feels broken. However, he makes the mistake of catching romantic feelings for her. Unfortunately, the object of his affection doesn't return his emotions with the same intensity.

The man places his love interest up on a pedestal and prioritizes her needs above his own ("I put you on top"). The narrator then realizes that he must retreat from her and take care of his own needs first. The song is widely regarded to be inspired by The Weeknd's 10-month relationship with singer Selena Gomez in 2017.

12. "It Ain't My Fault" by Brothers Osbourne

Blame falls like dominoes from one thing to another in this catchy 2016 country tune. The narrator admits that a "lotta wrong got done" but completely denies responsibility for scandal. Instead, he claims that if you're looking at him as the guilty party, then you've made a mistake.

13. "Hard to Say I'm Sorry" by Chicago

We're not sure whether the fella in this 1982 soft rock ballad cheated on his significant other or betrayed her trust in some other way, but she is expressing that she needs a break from their relationship as a result of his actions. In an effort to make amends, the protagonist attempts to repair their relationship with an apology for his errant ways. He doesn't want her to leave. Coming clean with his misdeeds and a heartfelt expression of regret has made him vulnerable, as he doesn't want to lose their longstanding love relationship.

14. "Paradise by the Dashboard Light" by Meatloaf & Ellen Foley

For the man in this iconic 1978 rock opera single, one passionate lapse in judgment leads to a lifetime of unhappiness. In the song, a couple of 17-year-olds are on a date at their favorite parking spot. They are in the guy's car and experiencing "paradise by the dashboard light" when the guy pressures his girlfriend to have sex.

She prefers to sleep on the decision. However, when the narrator implores her to go through with it that night, they agree to consummate their relationship only when he promises that he will love her, marry her, and never leave. Of course, she becomes pregnant, and the narrator's fate is sealed.

Years later, the man wishes (only partially in jest) that he could undo the mistake they made that night:

So now I'm praying for the end of time
To hurry up and arrive
'Cause if I gotta spend another minute with you
I don't think that I can really survive
I'll never break my promise or forget my vow
But God only knows what I can do right now
I'm praying for the end of time.

15. "Past Mistakes" by Goo Goo Dolls

Sometimes you just have to stand back and let the people you love make hard mistakes, learning by experience. It's tough to watch.

The young person at the center of this 2022 rock ditty is filled with hidden rage, and they are scarred by their past mistakes and tragedies. They don't trust the narrator (who seems to be a parent or important authority figure). Sometimes the young person doesn't speak for days, as they are lost in their own world.

For now, the narrator decides to back off. He gives the youth some space to experience the pain on their own —"You're growing through what you're going through"—because so far they haven't been willing or able to learn from their errors.

16. "Monster" by Justin Bieber & Shawn Mendes

Pop singers Justin Bieber and Shawn Mendes each grew up in the public eye—certainly not an easy thing to do. As teenagers are prone to do, they each made mistakes. However, their public profiles added to their stress and embarrassment. The young musicians' cringeworthy blunders became fodder for the tabloids.