It’s a long-running joke in our house that my wife thinks I only listen to depressing music and, well, she may have a point. So let’s infuse a little of that gloom into this most romantic of days by celebrating some of the most miserable “love” songs every written.
“Falling in Love” by Lisa Loeb
Delicate acoustics, Lisa Loeb’s sweet alto and the story of a woman who “wanted to be a cowboy” falling in love with a man who “walked in crooked with the clear blue eyes.” All the elements of a timeless romance are here, so what could possibly go wrong? Well, after a meet-cute that memorably involves a motel pool, things sour quickly as our cowgirl finds herself abandoned by the wild man that she could never tame and who disappears from sight, only to call home in the middle of the night from three time zones over. Most importantly, there has never been a sadder use of the phrase “falling in love” than in this song’s chorus which plaintively claims that “the time between meeting and finally leaving is sometimes called falling in love.” Ouch.
“Miss You Love” by Silverchair
In what is undoubtedly the prettiest song on ’90s alt-rock staple Neon Ballroom, singer Daniel Johns sings, “I’m … not too sure how it feels to handle every day. And I miss you, love.” It’s beautiful. Except that “Miss You Love” is not really a love song at all, but rather a song about Johns’ inability to maintain a long-term romantic relationship and his growing frustration with fans who claim they love him but who can only really love the idea of him. That sentiment comes through a little more clearly as the song moves along and he sings, “remember today, I’ve no respect for you,” and then, “I love the way you love but I hate the way I’m supposed to love you back.” That seems healthy.
“Love Song” by Sara Bareilles
Everyone who was alive in 2007 knows this song and while those who only remember the title might assume it’s a proper love song, those who remember its lyrics—like the chorus’ refrain of, “I’m not gonna write you a love song because you asked for it”—likely assumed that, even though it’s defiant rather than tender, the song is at least about a person that Bareilles had been in love with. Wrong again! Turns out the song is about Bareilles’ frustration with her record label which was, get this, asking her to write a love song. She might not have followed through on their request but with “Love Song” she certainly landed the hit they were after.
“Love Affair” by Copeland
A title like “Love Affair” suggests a song about a passionate, illicit romance—your standard Nora Roberts stuff. That is, um, not what Copeland is providing here. “Love Affair” is actually a slow, somber song about a woman crying as she wonders why she got dumped: “Was your heart too soft? Was your love in vain? Was your kiss too weak? Were your eyes too tight?” That said, this song is sonically beautiful, albeit in a despondent kind of way (as many a Copeland entry can claim to be) and, unlike a lot of the other songs on this list, it actually ends with a small modicum of hope. During the song’s outro, Aaron Marsh offers encouragement to our broken-hearted protagonist, suggesting that, even for all the pain love can cause, it can be worth it to “lose your head just for your heart.” As Valentine’s content goes, that may not be a heart-shaped box filled with chocolates but it’s something.
“Love on the Rocks with No Ice” by The Darkness
With The Darkness, it’s never entirely possible to tell where the shtick ends and where the sincerity begins—although most likely there’s no sincerity at all—which led me to spend a solid ten minutes trying to figure out if the “on the rocks” of this song’s title is cancelled out by the “with no ice” leaving just “Love.” Or is the joke that love on the rocks with no ice is just love on the actual, destructive rocks? I don’t know and it doesn’t really matter. What does matter is that, sandwiched between lyrics like, “we’re not as close as everybody thinks” and “our lives just don’t correlate” this song has two—yes, two—separate breaks for guitar solos. God bless The Darkness. (Read that last line out loud for a fun Valentine’s Day statement.)
“Autumn Love” by Death Cab for Cutie
Ben Gibbard has a knack for writing songs that seem sweet and romantic and also feel incredibly dark. “Autumn Love” isn’t quite that dismal, but its lyrics certainly aren’t as bright and cheery as the song’s music feels. Between a remarkable amount of oh-ing, the song’s chorus continually states that “this autumn love is not enough,” which, well, that’s pretty straight forward, isn’t it? And in case that somehow wasn’t clear enough, Gibbard drives home how unsatisfied he is with the relationship at hand by singing, “I need to know depths deeper than the deepest of connections.” This is not a thing that people who are still in love say to one another.
“Love Love, Kiss Kiss” by Alkaline Trio
Alkaline Trio doesn’t really do love songs so, despite this song’s title, it shouldn’t be too surprising that it is almost exactly the opposite of a love song. (It’s also from an album named Agony & Irony so … yeah.) More than anything, “Love Love, Kiss Kiss” appears to be Dan Andriano’s anthem for people who aggressively celebrate Singles Awareness Day. The entire song is a paean for those who are aggrieved by unavoidable public displays of affection, most succinctly summed up by the lines, “Love love, kiss kiss. Blah blah blah. You’re making me sick. I wish you’d just stop showing off for the rest of us that no one wants to love.” Well okay then, Dan. And happy Valentine’s Day, everyone!