Opinion: Sorrowful and sweet songs to curate a satisfying Valentine’s Day playlist

A selection of songs to curate the perfect playlist for any and all Valentine’s Day occasions. Credit: San Jose Mercury News 2007 [Original caption: 300 dpi Daymond Gascon color illustration of red hearts emitting from radio.]

 Whether this Valentine’s Day includes gazing into a lover’s eyes over a fancy dinner or crying on the couch with a pint of ice cream for company, playing music is a cathartic way to honor one’s feelings. Because music is one of my sincerest pleasures, I have drafted up a love letter — or rather, tracklist — for the heart-filled occasion. 

“Andromeda” by Weyes Blood

Discovering new love and its innate vulnerability can be simultaneously sweet and scary. Weyes Blood captures this anxious hope with her angelic voice and ’70s-esque slide guitar, narrating an ascension into love on “Andromeda.” The song’s closing words can be read as a call to action for any hesitant, lovestruck listeners: For those who think a love affair is “meant to be,” Weyes Blood “[dares them] to try.”

“Kiss of Life” by Sade 

This ode’s sensual beat, jazzy piano and smoky, luxurious lead vocals are sure to soothe listeners into a dreamlike state. Sade’s enigmatic lyrics — which chronicle an angel by her side and a sky “the color of love” — hallow romance’s undefinable, mystic quality. Surely there is something magical about a connection powerful enough to be a “bridge” between hearts, an affection so strong that the world can feel your heartbeat. Perhaps most of all, the titular lyric, “kiss of life,” venerates love’s vitality and ineffability. 

 “You’re a Big Girl Now” by Bob Dylan

“Time is a jet plane, it moves too fast” — from recalling love’s first flush to bitterly speculating about finding his former flame in someone else’s room, Bob Dylan recounts the emotional realization of a storied love affair’s end. Listeners attempting to move on from a decaying romance will relate to Dylan’s wail that he’s “back in the rain” while his ex-lover stands securely “on dry land.” 

Clearly, Dylan’s lyricism is praised for good reason: What better captures heartbreak’s physical agony than his cry of “a pain that stops and starts like a corkscrew to [his] heart” since being separated from his partner? But it’s his indistinguishable voice, blazing with unbridled emotion, that clinches the song’s intensity.

“Lover, You Should’ve Come Over” by Jeff Buckley

With its somber harmonium notes and slowly strummed, jangly guitar chords, “Lover” resounds with a wistful melancholy. Rife with poignant imagery of a “lonely room” with an open window letting rain in, this song vividly reflects Jeff Buckley’s heartbreak as he struggles to let go of a “good love” gone wrong. 

Filled with regret at having been “too blind to see the damage [he’d] done” and unable to resist wondering where she is now as he “burns” for her “sweet return,” Buckley aptly conveys a breakup’s lingering grief; as his vocals soar to the bridge, he repeatedly cries that “it’s never over.” Still, the breathtaking ballad suggests that there is something incredible in loving someone so deeply, regardless of how badly things end.

“The Beautiful Ones” by Prince

Prince may be largely remembered for his sexy, funk-infused tunes, but his tender ballads — like “The Beautiful Ones” — reveal his aptitude for heart-touching songwriting. In this dreamy yet languished remembrance of those beautiful partners “you always seem to lose,” Prince urges a lover not to let him “waste [his] time” on a hopeless pursuit. 

Radiating ’80s nostalgia, Prince’s musing that “the beautiful ones hurt you every time” will strike a chord with any listener whose fantastical “visions” of love were crushed by another. As his voice transitions from heady malaise to frenzied yowling, Prince radiates lovelorn desperation; he may not know what he truly needs, but he knows that he wants his “baby, baby, baby.” A hopelessly hopeful romantic, indeed.

 “Valentine” by The Replacements

The Replacements’ lead singer-songwriter Paul Westerberg’s knack for writing clever, poignant lyrics is palpable in the punchy “Valentine.” He speaks for any unapologetic romantic as he wishes “upon a star that turns into a plane” — sometimes, love that seems so tangible just isn’t meant to be. 

Westerberg’s declaration that if his beloved were a pill, he’d “take a handful at [his] will” brilliantly captures the drug-like obsession of hopeless infatuation. Expanding upon the motif of desire’s addictive quality, he wonders if his lover is similarly “strung out on some face” that is not his own. 

Despite his loneliness, Westerberg has hope for getting by without his obsession. While admitting that “tonight belongs” to his infatuation, he eventually asserts that “tomorrow’s [his].” So, feel no shame in being hungover on impossible visions of a crush this Wednesday. 

 “Valentine” by Fiona Apple

Another song called “Valentine”? Beyond its seasonable title, Fiona Apple’s account of unrequited love is piercing. Throughout the song, her desperation builds from lamenting a failed attempt to send a valentine “via pantomime” to frustratedly bemoaning that she’s “too dull” to grow up and let go of her all-consuming obsessions. 

Perhaps most heartrending is the chorus; against jarring piano notes, she desperately repeats, “I root for you, I love you,” capturing the incurable ache of truly caring for someone whom you know is “watchin’ someone else.”

“Here, There, and Everywhere” by The Beatles

Within The Beatles’ sprawling discography of love songs, the Paul McCartney-driven “Here, There, and Everywhere” stands out for its beautiful melody and trademark harmonies. The song coyly describes a true love with some kind of elusive quality — a love for which you can’t “deny that there’s something there.” 

There is no better song to commemorate a love that “never dies” than this ballad, which luxuriates in the little moments that truly encompass an incomparable relationship. After all, being “here, there, and everywhere” for one’s significant other is the purest expression of affection. 

“Love” by The Sundays

Regardless of relationship status, loving oneself is essential. On this track, lead singer Harriet Wheeler encourages anyone listening to “love [themself] like no one else,” as romance can be annoyingly fickle at times. 

If Valentine’s Day unearths anxiety that “you don’t have a clue about life,” find comfort in Wheeler’s airy voice and inspiration in her self-assurance that despite her own uncertainties in life, “there’s something [she deserves]” — joyous, unabashed love.