More Than a Breakup: A Playlist for Love Lost, Regret, and Hope

The Songs That Understand

Love, in its purest form, is simple. Its absence, however, is one of the most complex and multi-faceted human conditions. A song about lost love is rarely just about a breakup; it’s a story of regret, a glimmer of hope, a pang of disappointment, or a nostalgic look at what might have been.

As a songwriter, I’ve always been drawn to these complicated emotions. Many of my own songs, like "Next Time I'll Be Better," live in that space of reflection. To explore this, I’ve curated a collection of songs that perfectly capture the different shades of a love that’s lost, unrequited, or just out of reach. Here's a look at the emotional journey we'll explore.

Songs & Feelings

A curated list of songs and the specific emotions they evoke.

Song Title	Artist	The Feeling It Captures
"This time I'll Be Sweeter"	Angela Bofill	Hopeful Regret
"Next Time I'll Be Better"	Kevin I.	Taking Responsibility
"I Can't Make You Love Me"	Bonnie Raitt	The Unrequited Ache
"Same Old Lang Syne"	Dan Fogelberg	Bittersweet Nostalgia
"If I Love Again"	Kevin I.	The Lingering Question

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The Hopeful Regret: A Promise to Do Better

Sometimes, a love ends not with a bang, but with the quiet, aching realization that you could have done better. A perfect example of this is Angela Bofill’s soulful classic, “This Time I’ll Be Sweeter.” It’s a song about learning from past mistakes and making a heartfelt promise to be better in the relationship. It’s not about bitterness; it's about a mature, hopeful regret.

It’s this same sentiment that I poured into my own song, “Next Time I’ll Be Better.” As the only song in my catalog for which I composed both the music and the lyrics, it’s incredibly personal. It’s about looking back with honesty and making a promise to yourself for the future.

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The Unrequited Ache: The Love You Can’t Force

There is perhaps no more vulnerable place to be than loving someone who can’t love you back. For me, no song in history has captured this with more devastating beauty than Bonnie Raitt’s “I Can’t Make You Love Me.” The sparse piano, her raw and weary vocal—it’s the sound of surrender. It’s a masterpiece of quiet heartbreak.

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The Nostalgic Encounter: A Ghost from the Past

What happens when you run into an old flame years later? Dan Fogelberg’s “Same Old Lang Syne” is a cinematic short story set to music. It captures that bittersweet mix of nostalgia, curiosity, and the sad acceptance that your lives went in different directions. The closing saxophone solo feels like a sigh for a past that’s truly in the past.

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The Lingering Question: What Happens After?

After the initial pain, there’s often a quiet, contemplative period. It’s the space where you’re left with the memories and the lingering question: what now? The Commodores’ “Still” lives in that space beautifully.

It’s also the question I explore in my own song, “If I Love Again.” It’s a classic power ballad, and its enduring popularity tells me that this quiet, hopeful question is a universal one. It’s about wondering if you can open your heart again after it’s been broken.

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The Enduring Hope: A Love That Is Found

While we’ve explored the complexities of lost love, it's the hope of a steadfast, supportive love that we all ultimately seek. Cyndi Lauper’s “Time After Time” is the perfect anthem for that feeling. It’s not a song about a breakup; it's about the unwavering promise to be there for someone, no matter what. It's the beautiful, reassuring answer to the questions and heartaches posed by the other songs on this list.

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Build Your "Love Lost" Soundtrack

These songs are the perfect starting point for your own personal playlist. Find them on your favorite streaming service and let them be a source of comfort and reflection.

What song has helped you through a moment of lost love? I’d be honored to hear about it in the comments.