"Why waste your time worrying about it?" demands nearly everyone I have ever made the mistake of confiding in. "The past is past. Nothing you can do about it now."

This little morsel of non-insight has been dispensed to me by friends, relatives, and relative strangers for lo these interminable years of what one can only laughingly call my adult life. The purported wisdom: Don't fret over things you can't control. To which I say: What the hell else are you supposed to fret about? The whole point of irrational anxiety is that it's not rational.

There are plenty of real-world applications for irrational feelings of regret, remorse, and dread. But the all-time champion has always been romantic disappointment: things done to and by you, by and to people you loved exuberantly or insufficiently; ways you failed to express or conceal that love; terrible words spoken; perfect words unspoken; mistakes, missteps, misunderstandings; conversations too long delayed; steps too soon taken; habits pampered; work neglected; and, above all, the haunting awareness of having squandered a miraculous human synchronism and not being able to viscerally remember why it seemed so necessary to bail or to be bailed on.

It is good and even valuable to spend time pondering the lapses listed above—not because it helps you never make mistakes again (you'll just find new ones to make, because you are as complex as a panda), but because it keeps you awake and alive to the precariousness of love.

Someone will always be around to give you the old "regret is a useless emotion" argument. But those people are probably libertarians or sociopaths. And some people really are bad at moving on from things. In his 1951 classic The Wisdom of Insecurity, Alan Watts very shrewdly observed that "pain and the effort to be separate from it are the same thing." So, as Dorothy Parker once wrote, you might as well live.

Now, you're always free to go for a run or acquire a new company in an effort to sublimate your blues—and I recommend those things too, absolutely. But I'm also here to advocate for not sublimating those blues. I'm here to advocate for staring into the abyss of them until they have no choice but to stare back.

The ideal tool to facilitate a power wallow in the mud pit of romantic agony is music. Sad songs, as Elton John once memorably sang, say so much. (Though, obviously, his best sad love song is "I Guess That's Why They Call It the Blues.") As for what makes a good sad song, everyone's different. I recently learned that a friend didn't think "For No One" was sad but did think "The Long and Winding Road" was. Madness.

Everyone has certain songs that will lay them out, and often it's particular to the person and isn't shared widely. So individual results may vary. But my playlist—the best songs to listen to when you're brokenhearted (FACT)—is below. It's my gift to you. As Valentine's Day presents go, it's a lot more useful than a heart-shaped box of Russell Stover chocolate-covered goo.

"Tar the Roofs"—Radar Bros.—The Singing Hatchet

A short, slow, dusky dirge that leaves spaces between its enigmatic lines that you can fill with your own melancholy projections. Then the harmonies come in on the second verse, and you're finished.

"Skating at Night"—Amy Blaschke—Amy Blaschke

So chillingly solitary, you can almost see your breath. "It makes me sentimental," indeed.

"Hawaiian Baby"—the Spinanes—Imp Years

Some memories are extra painful because they're incomplete without an audience. Rebecca Gates runs a slide show of discarded photos and dislocated fragments that add up to a simple, sad, universal understanding: "It's my heart and it doesn't fit yours." But the real killer is in verse three.

"Hope She'll Be Happier"—Bill Withers—Just As I Am

Bill Withers's howl is a perfect evocation of pre-dawn surrender after a long, dark night of camouflaging sadness as rage and indignation.

"Smoke and Mirrors"—the Magnetic Fields—Get Lost

People usually think of irony as armor against human feeling, the way they used to think of synthesizers as soulless. Stephin Merritt has the gift of enlisting his impeccable craft to capture the way that armor drags you to the bottom of a sea of ungovernable feeling, a simple descending keyboard line accompanying you on your way down. Contrary to popular opinion, being clever only makes it worse.

"Accidentally Like a Martyr"—Warren Zevon—Excitable Boy

The steel guitar and "mad love, shadow love, random love, and abandon love" threaten to disrupt the mood by making you fear someone slipped some Eagles into your maudlin goulash. But the baleful ache in Warren Zevon's voice as he reaches for the high note brings you back, just in time for one of the great self-pity couplets of all time.

"Can't Fight It"—Bob Mould—No Alternative

My vote for Bob Mould's most heartbreaking song takes place in an aftermath, but keeps striving to reach backward to a moment before, when one person had to be the one who finally said what both people knew all too well. The Sugar-esque drums and synths don't come in until the words and acoustic guitar have said everything there is to say, grammar be damned.

"Stockholm Syndrome"—Yo La Tengo—I Can Hear the Heart Beating As One

James McNew does his finest Neil Young in this protest song against the impulse to give up on romance after another disappointment. "And I know you know it makes me sigh, I do believe in love."

"Dance Slow Decades"—Angel Olsen—Burn Your Fire for No Witness

A pas de deux between hope and despair. "I can see you dancing, if you'd just take the step," Angel Olsen sings, her throat threatening to constrict. "Dance slow decades toward the sun, even when you're the only one."

"Behind the Garage"—Eric's Trip—Love Tara

It's really just a whisper of a song, with a desolate little dying fall of an acoustic guitar figure to introduce the chorus. Twenty-five years later, I still don't know what he did behind the garage. I just know it was sad.

"Soul and Fire"—Sebadoh—Bubble & Scrape

Occasionally I look up and realize that this song has been on repeat in my subconscious since 1993. I know perfectly well that it embarrasses and enrages many people, but the audacity of singing "I think our love is coming to an end" at the climax of a chorus has never failed to get me.

"The Letter"—Kristin Hersh—Hips and Makers

This song is a letter. The words are jagged from trying to keep up with the tempo of thoughts rushing through a mind desperate from loneliness and related afflictions. Her brass voice starts small and grows wilder before signing off "Love, Kristin. P.S. Keep them coming." No one portrays life-threatening distress like Hersh.

"Midnight Cowboy"—John Barry—Midnight Cowboy Soundtrack

The stateliest melancholy I have ever heard.

"Plain Gold Ring"—Nina Simone—Little Girl Blue

The words are the words, but the sorrow lives in Nina Simone's high, wordless notes, and in the space between the simple piano figure and the distant snare drum.

"You Never Wanted Me"—Jackson C. Frank—Blues Run the Game

A perfect statement of the self-pity and acrimony that invariably follows rejection and feels like strength, instead of its surrogate, bravado. You don't have to know that Jackson C. Frank died homeless, penniless, and forgotten at 56, or that schizophrenia felled his once-promising career, or that his entire body was riddled with burns from a fire at his school when he was 11 years old, to feel the anguish of this song, but knowing those things helps you appreciate the gentility of its English folk guitar lines, and the plaint of its melody.

"On Your Own Again"—Scott Walker—Scott 4

Scott Walker conjures more majestic desolation in under two minutes than lesser musicians manage to create in their entire lives. You can really swoon inside the cloud of this song.

"Everybody's Best Friend"—Hazel—Toreador of Love

An impeccably sad song by Portland's finest. There's a strain of youthful bohemian romantic poetry in the refusal to let go of someone who wants to be let go of, but it gives way to the glorious simplicity of the yearning refrain, repeated three times: "I wanna wake up in my own bed again."

"Let the Wind Carry Me"—Joni Mitchell—For the Roses

"I get that strong longing, and I wanna settle and raise a child up with somebody," sings Joni Mitchell, who is usually the quintessence of self-reliance. She sings the line that follows like she's trying to convince herself: "But it passes like the summer, I'm a wild seed again, let the wind carry me." You can hear that she almost means it.

"In Spite of Me"—Morphine—Cure for Pain

An inversion of the familiar "I never loved you anyway" song, Mark Sandman's hushed growl offers an act of supplication, a statement that he'll always be in the corner of the one who left him behind. Far from being bitter or passive-aggressive, he's "proud to have been a step upon your way." Same chords as Led Zeppelin's "Going to California," but it contains more real human feeling than that band's entire discography.

"Verdi Cries"—10,000 Maniacs—In My Tribe

What can I tell you? Some of us will always be 14 years old. Give me a piano, a cello, and a woman's voice, and I'm ruined. "The opera, the stolen tea, the sand drawing, the virgin sea—all years ago."

"Just Another High"—Roxy Music—Siren

Though you don't really associate Bryan Ferry with human emotion, this is him at his most forlorn and abased. The song is the quintessential statement of romantic self-pity, addressed to a beloved who probably isn't even listening since she obviously doesn't even care and never did. And yet, the singer, even when crouched in a posture of lovelorn prostration, can't help looking up through the lock of impeccable hair that falls perfectly over his tear-glistened eye. The pose doesn't undermine the feeling—it consecrates it.