Aching For You: 8 Songs For the Lovelorn on Valentine’s Day

Many people will be come home to a bouquet of roses tonight or will gaze across a candlelit dinner into the eyes of that special someone. For these lucky souls, Valentine’s Day is cause for celebration and an excuse, as if one is needed, to throw a little kindling on the romantic fire. For many others, however, Valentine’s Day is a kind of a dirge, a painful reminder of someone or something that is missing. Some of these individuals are deep in the ravages of a recent breakup and all the intensity that comes with it. Some are quietly enduring the dull loneliness of long unrequited love. Still others are simply ambling along alone in the world, left to fend for themselves in life’s vast existential plains. These tender spirits often watch Valentine’s Day from the sidelines.

For the heartbroken and lonely, I’ve compiled a list of eight songs. These reflect the other side of love and might be a good soundtrack for anyone who feels removed from today’s celebrations.


1. You Don’t Know What Love Is.

 This standard, composed by Don Raye and Gene de Paul, was originally written  for an Abbot and Costello movie. It went on to become one of the most popular tunes in the Great American songbook. It has one of my favorite lyrics of all time: “ You don’t know how hearts burn for a love that cannot live yet never dies.” That pretty much says it all.  In this clip, Chet Baker’s soft intensity soulfully conveys the deep ache within the song.


2. Deep Song

While “Good Morning Heartache” is certainly Billie Holiday’s quintessential anthem to pain, “Deep Song,” penned by George Cory and Douglas Cross, is equally as wrenching.



3. Everything Must Change

Love, like everything else, is subject to the laws of impermanence. I’ve always loved Karrin Allyson’s recording of this haunting composition by Bernard Ighner.


4. Inside a Silent Tear

Blossom Dearie penned this delicate and wistful tune. Carmen McRae is my all-time favorite jazz vocalist and does a beautiful job with this.


5. I Can Explain

Although I’ve featured this song in other posts, it’s most definitely worthy of inclusion here. Raw emotion from my hero Rachelle Ferrell. The perfect song for those days when you just have to weep.



6. A Thousand Beautiful Things

Although there is much buzz at present about Adele’s break-up inspired CD “21,” Annie Lennox’s 2003 recording “Bare” is the ultimate break-up album. “A Thousand Beautiful Things” is a fitting requiem for the end of a relationship.



7. Both Sides Now

Joni Mitchell has been a lifeline through many a heartbreak in my life. While there are so many of her songs that would be fitting for today, I guess I chose “Both Sides Now,” because it best communicates my senibilities in the here and now: “I really don’t know love at all.” This is Joni in all her majesty. Sigh.



8. Lush Life

No song in history probably encapsulates heartache and sadness as well as this classic. Composed and performed here by none other than the great Billie Strayhorn.



A few closing thoughts:

 Although I don’t have a significant other, I choose to view Valentine’s Day as a holiday for all kinds of love and tonight I will celebrate by making a nice meal for family and friends. While the day may be sad for some, we each have a choice as to what we project on it and how we deal with it.

Valentine’s Day is ultimately what we make of it.



The comments section, as always, is wide open. I’d love to hear your thoughts about other songs that might be included on this list or anything you have to say about Valentine’s Day in general.