Tomorrow is Valentine’s Day, and what better way to celebrate the favorite holiday of florists and over-sized teddy bear manufacturers than with some sappy, romantic, feel-good love songs?

Well, I can think of one thing better: a playlist of songs about heartbreak and loneliness.

I consider myself a blessed man on Valentine’s Day. I have a terrific wife (this will be 11 straight years of having her as my Valentine!), and four adorable children (three of whom are little girls whom I consider my Junior Valentines). So there’s certainly no shortage of love in my life around this time of year. I’m very grateful.

But relationships in this world are hard. And messy. And fragile. And I know that many people see February 14 not as a time to go buy roses for a loved one, but as a time to be reminded of past failures. Or broken relationships. Or love yet to be discovered.

So in recognition of the difficulty of love and the scars that many carry, I’m taking this occasion to highlights some songs that explore the themes of loneliness and loss in a particularly powerful or profound way. I’m not trying to be depressing or to kill off an otherwise cheerful holiday. I just happen to think that musical artists have an uncanny ability to help us see the brokenness around us. And if we really love people (which is the whole point of this holiday, right?), we’ll want to be as fluent in the language of that brokenness as we possibly can be.

So, let’s get to it.

1. Death Cab for Cutie, “Cath…”

This song about a reluctant bride headed for the altar vividly depicts the inner turmoil of someone who is entering a relationship for all the wrong reasons. This one line captures the tension beautifully: “As the flash bulbs burst, she holds a smile / Like someone would hold a crying child.” But perhaps the real gut-punch in this song comes at the end, as the songwriter confesses, “I’ve had done the same as you.” Indeed, most relational mistakes are probably more universal than we realize.

2. David Ramirez, “How Do You Get ‘Em Back?”

It’s supposedly better to have loved and lost than never to have loved at all. But that’s hardly comforting for someone suffering the effects of a relationship that has recently gone off the tracks. Loss hurts. Which is why David Ramirez channels the desperation of a lover left behind to ask, “How do you get ’em back when they say this is the last time? / How do you make it last when they’re gone?”

3. Middle Brother, “Million Dollar Bill”

This is sort of an ironic take on the theme of being left behind. It’s certainly sad. But at the same time it’s resolute (in a way that’s almost humorous). Heartbreak can drive someone to extreme measures such that in the end, becoming a president, an astronaut, or a movie star may not seem all that far-fetched.

4. Ryan Adams & the Cardinals, “Hard Way to Fall”

Few people are better at the art of sad songs than Ryan Adams. (He’s actually pretty good at the art of happy songs…and just about any other kind of songs, frankly). Anyway, this song reminiscing about a woman who has moved on always gets me at this line: “See her smiling at him? That used to be me.” Indeed, romance can be mighty fickle. So if you’ve been fortunate enough to know long and happy years of commitment and love, don’t take it for granted.

5. Lindi Ortega, “Ashes”

I came across this song not too long ago and was immediately caught up in its old-timey twang that is almost Dolly Parton-esque. (Okay, that might be a terrible comparison.) Still, this longing plea not be left “in the ashes of your memory” is perfectly expressed by Ortega’s vintage vocals. It’s a modern song but feels like blast from the past.

6. Dr. Dog, “Lonesome”

Some heartbreak songs are reflectiveive and sad. Others are defiant and borderline angry. This track certainly falls into the latter category. (The refrain “Get out of here! Leave me alone!” is just one small hint…) It’s filled with emotion and energy, and this live recording captures quite a bit of that.

7. The Swell Season, “I Have Loved You Wrong”

“Forgive me lover, for I have sinned. I have done you wrong.” Now there’s a way to start out a song, eh? This heartfelt confession of past misdeeds yearns with anticipation for a future restoration and rekindling of love. But the song gives no indication that such a future is forthcoming. Thus, we’re left with nothing more than apologies, regrets, and a haunting sense of helplessness. In the end, we’re all powerless to erase the past.

8. Lucero, “My Best Girl”

We couldn’t have a heartbroken Valentine’s playlist without Lucero. And what’s more heartbreaking than for a man to reach the point of such relational disillusionment that he resigns himself to saying, “The only girl a boy can trust is his guitar”?

So there you have it. The moral of the story? Not everyone is equally excited for Valentine’s Day. So enjoy your loved ones and eat lots of chocolate. But at the same time, let’s be kind to the many people suffering through another painful reminder of heartbreak and loss.

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