The Breakup Playlist Vol 1: The Sadness

Over the past year I’ve watched as countless friends experienced unprecedented heartbreak in relationships. There are any number of factors you could blame, but it doesn’t diminish the pain of parting ways. This is for them, for us…

I hope you’re not here in the hope I’m going to tell you “heartbreak is hard, but chin up, you’ll get through it and come out the other side a stronger person.” That’s not why you’re here, to read about hope, is it?  You’re here to commiserate, to hear someone say “getting your heart broken f*&$ing hurts.” The pain is, well, it’s indescribable, but let’s try to put that pain into words for a second shall we? It feels something like someone pulling your actual beating and bloodied heart right out of your throat. They’ve reached their fist right down your esophagus and torn through a few vital parts of your body to grab hold of your internal life force and rip it out, painfully and slowing and without consideration for your health, mental or physical. And it happens when it seems time is standing still, and there’s no end in sight. Just pain. Does it sound like I got that right? A good definition of the agony of heartbreak?

The thing about heartbreak is no two experiences are ever the same. It’s hard to try and offer advice to anyone on that basis. Some heartbreaks are because of you, some have nothing to do with you. Heartbreaks can hit you like a mack truck in the middle of the night or slowly chip away at you until a small crack turns into a shattered person. But, even if the heartbreak is experienced with the same person again and again or under similar circumstances, it starts a whole new hurt and a whole new healing process. That’s just a long way of saying I’ve never heard anyone say they enjoy heartbreak.

In my many years of dating, and after several rather epic heartbreaks, I have discovered one thing to be absolutely true and it goes a little something like the following.

My heart breaks, and then it heals in three chapters. These chapters can come at different times for different people, but each one has always had a dedicated soundtrack to healing, a playlist if you will. And that’s what I want to offer today as a security blanket of sorts. These playlists have been developed over years of love, lust, loss and longing. The buckets of tears shed over this first installment could, rather embarrassingly,  fill an olympic sized pool. But this is what heart break is. Sadness.

So yes, my first chapter and Vol 1 of the heartbreak playlist series is all about the breakup chapter of sadness.

This first chapter for me is always the longest one. It’s that chapter where you think about every memory, dissect every perfect moment and seem to somehow forget all the bad things that ever happened. It’s the chapter where often times I’ll think it might not all be over. I might think there’s a chance. I might think I could have done things differently. It doesn’t matter if I ended it or he ended it, this pattern is always the same. The good memories, the rethinking of what could be different and the ridiculous notion that there might still be some chance of reconciliation.

The core of the playlist always remains the same. But, there are alterations based on memories with people, songs that have sentimental value for moments in the relationship, and so forth and so on. But, for sharing purposes, I’ve put together the classics that work for each and every heartbreak. These are the songs that let you cry. They’re the songs that whisper “you aren’t alone” as you lay in the middle of your bed in the dead of night and wonder if you’ll ever move to the side to make room for someone new in your life. These are my songs of sadness and I invite you to slip on your headphones, in a room by yourself and just get lost in the melodies, the beautiful heart wrenching lyrics and the soulful swings of every romantic instrument ever invented. Ladies and gents, just cry, unashamedly. Heartbreak hurts. There is no way these songs could have been written otherwise.

There are exactly 100 songs on this playlist. That’s 7 hours and 7 minutes of soul searching. Play on shuffle or listen as I’ve ordered them. There is no right or wrong way here.

I’ll leave you and ready you for chapter two coming soon. I’ll also encourage you to submit additions in the comments section below, if there’s a song I’ve missed. Maybe one I’ve never heard of? I’ll gladly make this a list that grows as a community. And for the heartbroken out there reading this, you do you. Grieve like you need to, heal when you can. This is your time schedule, no one else’s and there isn’t a single solitary soul on this earth that knows, like you do, what went on in your life to make this heartbreak real. Just please know you aren’t alone, you never are when it comes to matters of the heart. It’s a universal hurt.

NOTE: This is a new series and it’s all around playlists that I’ve been making my whole life. I’ve been making them since I was a teenager and was recording songs to cassette tape from the radio. I thought it was high time I share the obsession. We’re starting with heart break because, well, it’s a universal feeling and probably the playlist that I’ve changed around, added to and subtracted from most over time. I have no affiliation with Spotify, it’s just the easiest way to share these things! 




  1. Danielle
    1st July / 7:32 am

    I have a song to add.

    Kodaline – all I want ❤️

  2. Jeanette
    1st July / 8:30 am

    Thanks great list and a lot of work
    A lot of the songs are uplifting also
    Well done xx💗💗

  3. Claire
    1st July / 8:54 am

    My go to sad song is always REM’s Everybody Hurts. Always cry my eyes out to that xx

  4. Amanda
    1st July / 2:43 pm

    Wasn’t making “mixed tapes” the best? Thanks for sharing this sadness list. Two songs that got me through heartbreak: “Quittin’ Time – Live at Ryman Auditorium” by Mary Chapin Carpenter and “And So It Goes” by Billy Joel.

  5. Leyna
    1st July / 5:39 pm

    Oh the Noah Reid cover! Classic heartbreak and yet joy! Epic work! ❤️

  6. 1st July / 7:15 pm

    Since you were so kind to share your heartbreak songs, here are some of mine:

    How can you mend a broken heart?- Al Green
    How Long Has This Been Going On?-Louis Armstrong
    Now At Last- Feist
    Low Rising- Glen Hansard
    Emotions- BeeGees/Destiny’s Child

  7. Elaine
    1st July / 8:41 pm

    Amazing playlist! You should add Bonnie Raitt’s ‘I Can’t Make You Love Me’, gosh, the pain!

  8. Kathy
    2nd July / 3:12 am

    Key songs here – Let It All Go, I Can’t Make You Love Me, and Both Sides Now. On REPEAT.

  9. Sandy
    3rd July / 4:40 am

    I Don’t Think About You, Kelly Clarkson. Powerful song. I love the list. Keep ‘em coming.

  10. 3rd July / 7:15 pm

    Oh my goodness, what an amazing playlist!

    Danielle |

  11. nina townsend
    20th July / 11:08 am

    Heart break for me has happened all too often…. my 20’s and 30’s were marred with love and losses. The only thing I listened to then was Joan Armatrading and Joni Mitchell.. such a beautiful play list … Nx

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