25 Songs About Regret

We all make mistakes in our lives. Some are probably too great that we end up regretting them for so long. What could we have done differently? What would the present look like if we only did the right thing?

We’re certain these questions are really difficult to face. Perhaps we may never find the answers to them, and all we can do is to ponder over or sing about them. Well, we found just the perfect songs to sing along to.

Here are 25 songs about regret that perfectly summarize your emotions.

Songs About Regret

1. Wishing It Was You

Artist: Connie Francis

Album:

Release Date: 1965

If there is ever one song about regretting ever letting someone go, this one would probably win the belt. The song is about getting married to someone you’re with while someone else holds your heart. The lyrics go;

“Tomorrow, when I’m walking down the aisle
I’ll try to hide my heartache with a smile
‘Cause when I look at him and say I do
In my heart, I’ll be wishing it was you”

Imagine that one day in your life when you’re supposed to be the happiest turns out to be the moment you regret the most. What a heartache!

2. Supermarket Flowers

Artist: Ed Sheeran

Album: ÷ (Divide)

Release Date: March 3, 2017

This next song is about regret or guilt and how we can turn it around and instead dwell on the good memories we are left with. Supermarket Flowers is a song Sheeran wrote for his grandmother, who passed away.

3. Never on the Day You Leave

Artist: John Mayer

Album: The Search for Everything

Release Date: April 14, 2017

I believe most of us who know John Mayer also know he dates high-profile celebrities and personalities. That’s why it’s kind of surprising to find that he actually has a few songs about regret. Never on the Day You Leave is perhaps the most heartbreaking one among those.

In fact, it took a while before he was able to perform it live. He says the lyrics are too emotional that it’s hard for him to actually sing them. The line he had a hard time with goes,

“She’ll fight for you like hell, then force herself to like some other man”

It was too hard for John to sing it that it took days for him just to record the vocals of the song.

4. Father and Son

Artist: Cat Stevens

Album: Tea for the Tillerman

Release Date: November 23, 1970

Cat Stevens’s song Father and Son is about trying to avoid making mistakes and regretting them afterward.

“But take your time, think a lot
Think of everything you’ve got
For you will still be here tomorrow
But your dreams may not”

Stevens wrote the song while imagining a conversation between a father and a son in the Russian Revolution. However, it’s safe to say that it’s also inspired by his relationship with his father, as the latter wanted him to continue the family’s restaurant business, but he chose a career in music.

5. Back to December

Artist: Taylor Swift

Album: Speak Now

Release Date: November 15, 2010

Aside from John Mayer, another popular artist whom we know dated a few celebrities is Taylor Swift (the two of them even dated a while back). We’re not being scornful, by the way, as this had blessed us with some of the best songs of all time.

One example of this is the popular track Back to December. It’s kind of surprising, actually, because we often hear Taylor singing about how her past relationships mistreated her. However, this song talks about how Taylor herself was careless with someone who loved her deeply.

6. Sorry

Artist: Justin Bieber

Album: Purpose

Release Date: October 22, 2015

The song title says it all. Justin sings about asking for forgiveness and a second chance. His personal regret over wronging a lover is well-expressed in the lyrics. However, some speculate that the song is more than just apologizing to a woman.

If you’ve been a Belieber since about 2008 to 2009, you’d know that Justin had some pretty rough years from around 2013 to 2014. Some say that Sorry is Justin’s apology to his fans and followers and wanting to start anew.

7. Baby Come Back

Artist: Player

Album: Player

Release Date: October 13, 1977

Baby Come Back is the number one song in the US in the first month of 1978. It talks about real events when Peter Becket’s wife left him to go back to England, and J. C. Crowley was mending a heartbreak. All of these emotions from the two founders of the band were channeled into the song.

8. 25 Minutes

Artist: Michael Learns to Rock

Album: Colours

Release Date: February 25, 1994

Here’s another song about regret at a wedding, but this time, it’s the perspective of a guy who wasn’t able to tell the woman that he loves her at the right time. The saddest part is, he was only 25 minutes too late, hence the title.

9. Lips of an Angel

Artist: Hinder

Album: Extreme Behavior

Release Date: April 3, 2006

A typical soft-rock tune from Hinder, their song Lips of an Angel quickly rose to fame after its release. What’s actually surprising about it is that it only took Austin Winkler and Cody Hanson, the band’s lead singer and drummer, respectively, about half an hour to write the song.

It’s about being with someone else despite the fact that you can’t let go of a former love and you regret ever letting her go. The lyrics on the pre-chorus explain that perfectly.

“My girl’s in the next room
Sometimes I wish she was you
I guess we never really moved on”

10. Nearly Witches

Artist: Panic! At the Disco

Album: Vices & Virtues

Release Date: March 18, 2011

Panic! At the Disco’s Nearly Witches, otherwise known as Ever Since We Met, actually has a sad backstory about how it’s made. It was the last ever musical idea the band came up with before two of their members, Jon Walker and Ryan Ross, left the band.

If you know the band’s history, you’d know that numerous rumors and speculations arose about the real reason why Ryan Ross and Jon Walker left. Perhaps the lyrics of the song capture what Brendon Urie and Spencer Smith felt about half of the band’s departure?

“Ever since we met
I’ve got just one regret to live through
And that one regret is you”

11. Tears in Heaven

Artist: Eric Clapton

Album:

Release Date: January 14, 1992

In 1993, Eric Clapton received nine Grammy nominations for this song. Out of all of these, he won six, including Record of the Year and Song of the Year. However, it’s not the awards that make this song remarkable but the story behind it.

Clapton wrote Tears in Heaven after the death of his son, Conor. Clapton’s son, unfortunately, fell out of the window of an apartment 53 floors up. This makes the lyrics even more heartbreaking than it already is.

“Would you know my name if I saw you in heaven?
Would it be the same if I saw you in heaven?”

After the death of his son, Clapton made a public announcement to encourage parents to install gates to avoid accidents such as this. No regret is more painful than losing someone you love dearly.

12. All Apologies

Artist: Nirvana

Album: In Utero

Release Date: December 6, 1993

Perhaps the only thing we’ll regret about this song is that all of us should’ve treated Kurt Cobain better. In Nirvana’s song All Apologies, people speculated that this is a fake apology from Cobain to numerous people who have contradicting expectations of how he should be.

This song, along with the track Rape Me, was the last single the band released. Four months after, Kurt Cobain committed suicide.

13. Molly

Artist: Lil Dicky feat. Brendon Urie

Album: Professional Rapper

Release Date: July 31, 2015

Maybe the adage stays true to its meaning; regret is always in the end. We tend to put things off, like changing for the better, until it’s too late for us to save what we could’ve had. Molly by Lil Dicky and Panic! At the Disco’s Brendon Urie perfectly sums this up.

“It’s the hardest rule to follow
I really wish that I could call you
You can find another me tomorrow
And that’s the hardest pill to swallow”

If you think those lyrics are painful, you should watch the music video.

14. Best I Ever Had

Artist: Vertical Horizon

Album: Everything You Want

Release Date: January 8, 2000

Here’s another song about feeling regret over losing someone you love. The painful part of it is that person was the best you ever had. The lyrics combined with the melancholic soft rock arrangement make the track a really heartbreaking song to listen to.

15. When I Was Your Man

Artist: Bruno Mars

Album: Unorthodox Jukebox

Release Date: January 15, 2013

Every word in Bruno Mars’s When I Was Your Man describes pain, unlike any other song. Mars even went on to admit that this song is really special and emotional to him as it described a very personal experience when he loved a girl so much, but they still broke apart.

“I should’ve bought you flowers
And held your hand
Should have gave you all my hours
When I had the chance
Take you to every party ‘cause all you wanted to do was dance
Now my baby’s dancing
But she’s dancing with another man”

It’s just really a different kind of pain and regret when the person you loved the most is now happy with another person.

16. How to Save a Life

Artist: The Fray

Album: How to Save a Life

Release Date: March 26, 2006

It’s about a real-life experience of Isaac Slade, the band’s lead singer. He had a quick encounter as a mentor for teenagers who struggle with depression, drugs, or other substances. One kid, in particular, lost his best friend and was suffering from depression.

The kid’s friends and family were trying all sorts of approaches and strategies to help him, but none of them seemed to be able to save the boy since, well, there’s no manual to saving a life. The lyrics of the song hint to regret about losing someone when there was a chance, albeit small, to reverse the results.

“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”

17. Stay with Me

Artist: Sam Smith

Album: In the Lonely Hour

Release Date: April 14, 2014

Stay with Me, or in fact, the majority of In the Lonely Hour is about Sam Smith’s love for someone who wouldn’t reciprocate his feelings. He even went on to say, as he received his awards, “Thank you to the man who broke my heart because you got me four Grammys.”

Stay with Me is about his one-night stand with this person. There is a hint of regret in a few lines of the song but the persona, despite knowing the relationship wouldn’t work, wants the other person to stay with him.

18. Photograph

Artist: Nickelback

Album: All the Right Reasons

Release Date: August 8, 2005

Photograph is the anthem for all our childhood memories we can never go back to. It’s about saying goodbye to the people and places you grew up with and in, and a slight twinge of regret of not being able to keep these relationships or connections alive and cherished.

19. Goodbye Yellow Brick Road

Artist: Elton John

Album: Goodbye Yellow Brick Road

Release Date: September 7, 1973

Bernie Taupin wrote most of the lyrics of Goodbye Yellow Brick Road. He says that it’s about longing for a simpler life. The song talks about living a successful and opulent lifestyle but regretting leaving the simplicity of the rural roots.

According to Taupin, it was largely about his life. He enjoys the success he currently has but sometimes dreads the limelight and the busy style of living. He wishes for a way that these two can coexist.

20. Hotel California

Artist: Eagles

Album: Hotel California

Release Date: February 22, 1977

Don’t be surprised to find this timeless song here. It is, in fact, a song about regret, among others. If you refrain from deciphering its hidden meaning, the surface layer of its lyrics actually regrets going to the place known as Hotel California.

It starts off as having a good time in the hotel with all its dancing and wine and pink champagne on ice. However, towards the end of the song, the lyrics go;

“Last thing I remember, I was
Running for the door
I had to find the passage back
To the place I was before
‘Relax,’ said the night man,
‘We are programmed to receive.
You can check out any time you like,
But you can never leave!’”

21. Like We Used To

Artist: A Rocket to the Moon

Album: On Your Side

Release Date: October 13, 2009

Going back to the arsenal of break-up songs, we have Like We Used To. It’s about longing for the person and regretting the break-up even now that she’s with someone else. It even goes so far as to ponder whether or not the new guy can love the woman like the way the persona in the song did.

22. Vincent

Artist: Don McLean

Album: American Pie

Release Date: February 1972

There are some things you can still fix in this lifetime, but there are those that you’ll regret for the rest of your life because it requires the impossible act of turning back the time. That pretty much sums up the inspiration for this song.

It’s a song written by Don McLean on a paper bag, of all things, about Vincent Van Gogh. The Dutch painter was often pictured as a social outcast and was sometimes even branded as crazy.

No one can deny the beauty of Van Gogh’s painting, as well as McLean’s song, especially in the lines;

“And when no hope was left inside
On that starry, starry night
You took your life as lovers often do
But I could have told you, Vincent
This world was never meant for one as beautiful as you”

23. Jealous Guy

Artist: John Lennon

Album: Imagine

Release Date: November 18, 1985

Aside from his hit single Imagine, another song from the same album that really pulls the strings of our hearts is Jealous Guy. Lennon was a bit regretful about his behavior with Yoko Ono, as he was very possessive of her.

24. Careless Whisper

Artist: George Michael

Album: Make It Big

Release Date: July 24, 1984

While the story of the song was entirely fictional, it still speaks of regret. It’s about feeling guilty of ever asking someone you admire to dance with you because, well, you don’t know how to dance.

However, a deeper layer of the song is actually about losing someone because the persona had an affair with another woman. Whether you admire the lyricism or not, you have to admit that this song has one of the best saxophone solos you’ve ever heard.

25. The Scientist

Artist: Coldplay

Album: A Rush of Blood to the Head

Release Date: November 11, 2002

Chris Martin explains that this song is about a scientist who spent most of his time working that he wasn’t able to take care of his girlfriend. He went on to say that it’s kind of weird that even though you’re faced with solving economic crises and environmental catastrophes, what would really get you down is if you’re not on good terms with the person you love.

“Questions of science, science and progress
Do not speak as loud as my heart”

The scientist in the song went on to regret taking his partner for granted and wanting to start again.

“Nobody said it was easy
It’s such a shame for us to part
Nobody said it was easy
No one ever said it would be this hard
Oh, take me back to the start.”

Conclusion

Regret is perhaps one of the most complex emotions we feel. That’s probably because it’s extremely difficult to face it because we can’t do anything about it, given the unidirectional nature of time.

Don’t worry. The next time you feel regret and you don’t know what to do about it, whip out this list of songs we prepared for you and have these amazing artists pour out your emotions for you.