Gwnewch y pethau bychain

30 Day Song Challenge – Day 27 – A Song That Breaks Your Heart

Today’s challenge invites us to share a song that breaks our heart. If I’d looked ahead on these challenges, I might have saved the Glen Campbell song I posted on Day 10 for “A Song That Makes You Sad” for this, and chosen a different sad song then. But since that’s under the bridge, here’s another song about heartbreak, and specifically about that moment in a long-term relationship when you realise things maybe aren’t going to work out in the end. I’m happy to say that it’s been a very long time since this song resonated strongly with me, but back when it did, it certainly was a time of tremendous heartache. Here’s Christine Lavin with “Katy Says Today Is The Best Day Of My Whole Entire Life”


30 Day Song Challenge – Day 26 – A Song That Makes You Want To Fall In Love


30 Day Song Challenge – Day 28 – A Song By An Artist Whose Voice You Love


  1. Jim Poltrone

    It’s a tossup between this and “If I Could Change Your Mind” — one of the few APP songs featuring a female vocalist (the late Lesley Duncan).

    • Lee Billings

      That’s definitely capable of more than one interpretation. Listening to it now, I hear someone trying to get his hooks back into a woman who finally managed to get out of a really bad relationship. Sylvia has her mother running interference for damn good reason.

    • Daniel Reitman

      I saw a documentary last year in which it turned out the woman who inspired Shel Silverstein thought of him as a friend

  2. Bruce Adelsohn

    Another no-brainer for me. Can never get through this without requiring a unicorn chaser.

  3. Patricia Jones

    Having children myself, hearing this song about parents attempting to cope with the death of a child breaks my heart everytime I hear it.

  4. Neill Mitchell

    Tori Amos’s cover of Tom Waits “Time” -- Gets me every time, and I’m not quite sure why.

  5. Stephanie Riehle Craven

    Certainly the first time I heard this, I wept. And even still it shakes me up to hear her sing about the love of a child. Joni Mitchell’s “Little Green.”

  6. T J Burnside Clapp

    I almost needed therapy after hearing this one. My oldest brother died at about the same age, and it tears me apart to think about what my parents went through. 🙁

  7. Bruce Adelsohn

    Also, this one. I can’t imagine being on either side of this situation.

  8. Paul Kwinn

    Yep, I might have swapped this with my “sad” song, too. But still, here’s Pete Grubbs, to depress you:

  9. Juanita Coulson

    “Hills of Ixopo” from ” Cry, The Beloved Country”.

  10. Dell Christy

    I still have tears when I listen to this.

  11. Laura Law

    Christine Lavin is one of my faves.

  12. Lee Billings

    I can’t listen to this without crying. The destruction wrought by well-meaning friends, and the joy turned to ashes.

  13. Laura Gallagher

    Since I already gave you It’s Quiet Uptown for that earlier one, I give you this one. I so wish I’d had this sort of support through our moves as a kid.

  14. Carolyn Fortuna

    This song makes me wistful and sad for simpler times with my family long gone.

  15. Heather Munn

    We keeping loosing too many good people, good musicians, good kids, to drug addiction:

  16. Manny Jacobowitz

    That’s a tough one. Could say Sondheim -- Send in the Clowns, or, One Hand, One Heart. Or Sunrise, Sunset from Fiddler, now that I’m a parent. But for sheer pain and need, imma go with one most of your friends won’t know already:

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