20 Heartfelt Songs About Second Chances

We’ve all had those moments in life when we’ve stumbled and wished we could rewind and redo. Let’s uncover together the music that celebrates learning, growing, and the beauty of a second chance.

The unique charm of these songs lies in their focus on second chances in love, they tug at our deepest emotions and infuse us with a sense of hope. So, stick around if you’re keen to dive into these tunes!

1. “Starting Over” by John Lennon

This is probably the first one that comes to mind when thinking of songs about second chances. “Starting Over” by John Lennon talks about a couple who break up only for one to regret the decision. The singer reminisces about the good times they had together and how they could start all over again, perhaps on a better note. Lennon’s timeless classic gives voice to the timeless desire to rewrite love’s narrative.

2. “Against All Odds” by Phil Collins

“Against All Odds” by Phil Collins talks about a person feeling completely worthless after their lover has walked away from their relationship. The heartbroken and jilted lover is so devastated by the experience that all they can do is cry about the situation. The song’s title becomes an apt metaphor for the protagonist’s belief that their lover’s return is unlikely, yet they’re willing to challenge fate itself for another chance.

3. “Every Road Leads Back To You” by Bette Midler

“Every Road Leads Back To You” by Bette Midler is not only about a desperate lover looking for a second chance, but also about a lonely friend looking for their missing companion. Midler’s powerful song communicates a sense of profound interconnectedness, highlighting an irreplaceable void that only the return of a loved one can fill.

4. “Make You Feel My Love” by Adele

“Make You Feel My Love” by Adele is a cover for a Bob Dylan song from the late 1990s and talks about the regret and feelings of desperation that creep in when your sweetheart dumps you. You know in your heart that you are the best mate for them but they refuse to see you in the same light. It’s also a plea to the partner to know them better before making any decisions. 

5. “Hate That I Love You” by Rihanna and Neyo

“Hate That I Love You” by Rihanna and Neyo has a slightly different theme from the songs previously mentioned in this list because it talks about falling for a person you know you shouldn’t fall for. This song might sound sweet the first time around but you will notice that it highlights the toxic undertones that some people experience in a similar situation. 

6. “Back To You” by Selena Gomez

“Back To You” by Selena Gomez has a similar theme as the previous one. You know your lover is not right for you but the heart wants what the heart wants. Gomez’s lyrics subtly sketch a canvas of her lover’s toxic traits, yet her inability to sever the ties speaks volumes about love’s intoxicating grip.

7. “Come To Me” by Mary J. Blige

“Come to me” by Mary J Blige is about a person who has been in a long-term relationship only to meet its abrupt end. There’s a lot of regret on the singer’s part and a strong desire to get back together. This emotive track is an ode to those who find their world incomplete without their beloved, transforming their yearning for a second chance into a symphony.

8. “If You Leave Me Now” by Chicago

Chicago’s “If You Leave Me Now” paints an affecting portrait of a lover on the verge of being left behind, and the impending transformation of their personal world. The lyrics unfold like a heartfelt plea, brimming with the conviction that their departing lover is irreplaceable. With a fervent appeal for a second chance, this song captures the desperation to mend what’s broken.

9. “The Long and Winding Road” by The Beatles

“The Long and Winding Road” by The Beatles is about a person who was left behind by their lover and getting them back is all they can think about. The singer talks about wanting to deny their feelings of love but just cannot do so and are secretly waiting for a second chance. It presents a secret yearning for another shot at love, an emotion that resonates with many hearts on the quest for second chances.

10. “Never Really Over” by Katy Perry

“Never Really Over” by Katy Perry has a similar theme as the one above but is more pronounced. Katy Perry and her ex-lover are not over each other even though they have broken up. If you ever tried to fight back the urge to get back together with their ex and failed miserably, this track will resonate with you.

11. “Still Loving You” by Scorpions

“Still Loving You” by Scorpions is a beautiful song about the feelings you have when you let real love slip through your hands and the regret that you feel when realization hits. The singer yearns for a do-over, a second chance to right the wrongs and relive love’s journey.

12. “Still In Love With You” by Sade

“Still In Love With You” by Sade is about a lover who has been left behind and spends the majority of their time overthinking how things could have been different. The song is a very sad rendition of heartache and sadness that follows after a breakup. 

13. “If I Should Love Again ” by Barry Manilow

Barry Manilow’s “If I Should Love Again” echoes the resilient spirit of a heart that clings onto hope, despite the odds. The song captures the essence of an individual who dares to dream of a reunion, knowing well the improbability. The track delivers the beautiful message – in love, a second chance can make everything better.

14. “Back To December” by Taylor Swift

“Back To December” by Taylor Swift is an apology song to a boy she has hurt in the past. The lyrics talks about the memories and the fun they had together and also touches on the darker side of her relationships. Rumor has it that Swift wrote this track about his past relationship with Taylor Lautner.

15. “Lips Of An Angel ” by Hinder

Hinder’s “Lips Of An Angel” spins a captivating tale of a man caught between his past and present. Despite being married, he finds himself yearning for his former love. This secret longing for a reunion echoes the heart’s persistence, as feelings for her refuse to fade. The song unravels the intricate web of emotions that binds us to our past, even as we journey into new phases of life.

16. “Never Gonna Let You Go ” by Sergio Mendez


“Never Gonna Let You Go ” by Sergio Mendez is all about a lover who has left behind their special one only to regret it in the end. The song is about glorifying what everything could have been while also realizing that the second chance might not come. It’s a poignant exploration of lost opportunities and the elusive nature of second chances.

17. “Take A Chance On Me” by ABBA

Taking a leap of faith, ABBA’s “Take A Chance On Me” is the voice of a person waiting in the wings for their love interest to notice them. It’s a refreshing contrast to the previous entries as it’s not about rekindling old flames, but about sparking a new one.

18. “Over and Over ” by Nelly & Tim McGraw

“Over and Over” by Nelly & Tim McGraw captures the heartache of watching a loved one drift away with someone else. It’s a raw reflection on lost love and the hope of a second chance, waiting for a big “yes” to turn their world around.

19. “Stay” by Lisa Loeb

“Stay” by Lisa Loeb is about a person who has been left behind by their lover due to their undesirable characteristics. Apparently, the singer has been very toxic in the past and is willing to change their ways only to have a second chance. The singer is ready to face their past mistakes and make amends, hoping that a transformation could pave the way for a second chance.

20. “Just Once” by Quincy Jones

Just Once” by Quincy Jones is about a person who has had enough of the “hot and cold phase” and just wants to make everything right one more time. The singer wants a second chance so they can put in extra effort by showing love and kindness.


Listening to songs about second chances will allow you to acknowledge some of your inner thoughts and feelings, especially if you have been in a similar situation before. All you have to do is put the headphones on and play any of these 20 songs and you will surely hear a story that might make you cry (sadness can be beautiful too).