Last year, I wrote about the best songs to listen to on Valentine’s Day, which featured numerous selections perfect for dancing the night away with your lover. This year, I’m taking a look at the opposite, assembling songs for all my fellow single warriors and hopeless romantics. Is it a more depressing list than last year? Absolutely. Are these songs still worthy of being blasted alone on Friday night? You bet. With that, let’s take a look at the best anti-Valentine’s Day playlist for 2025.
Fleetwood Mac – “The Chain”
It was hard to pick just one Fleetwood Mac song for this list given how most of their songs from the late 1970s are about their relationships falling apart. But no song is more emblematic of this than “The Chain,” the centerpiece of the 1977 best-selling album “Rumors.”
Built on a brooding dobro riff by Lindsey Buckingham, the song perfectly evokes the iciness of a breakup. The use of three singers — particularly the vocal interplay between Buckingham and Stevie Nicks in the chorus — hammers this home, sounding like two lovers breaking up through song. It’s the perfect post-breakup song, especially if that breakup unfortunately happened right before Valentine’s Day.
Smoking Popes – “Just Broke Up”
“Just Broke Up” by Smoking Popes, a 1990s pop punk band, is a song that’s not vague in the slightest of what it’s about. The song is built on the repeated line “just broke up with my girlfriend,” sung by frontman Josh Caterer in a way that sounds like he’s doing his best Morrisey impression. This is contrasted with an upbeat, slightly up-tempo arrangement highlighted by a smooth guitar solo.
Clocking in at only two minutes and four seconds, it’s the shortest song on this list. But it gets to the point and is incredible catchy, which is everything I want in a pop-punk breakup song.
Nazareth – “Love Hurts”
When I was putting this list together, this was the first song that came to mind. Originally released by The Everly Brothers, the Scottish band Nazareth turned it from a folk deep track to an emotional power ballad in 1974 with incredible results.
Singer Dan McCafferty delivers a vocal performance for the ages, belting the song’s emotional lyrics with great intensity. There are times where you can hear the raspiness of his voice increase to hit the high notes, adding even more emotion and pain to the vocals. You can practically hear his heart breaking during lines like “I know it isn’t true.” Combined with an echo-laden guitar arpeggio, this is an all-timer about love and heartbreak.
The Rolling Stones – “Memory Motel”
Remember that summer fling that you haven’t seen since then? Mick Jagger and the rest of The Rolling Stones reminisce on that in the 1976 deep track “Memory Motel.” Built on a slow piano-driven arrangement, Jagger sings about a girl he calls “Hannah Honey,” whom he spent the spring of 1975 with while the Stones retreated in Montauk, N.Y. He clearly misses her, but now she’s “just a memory of a love that used to be” and “a love that used to mean so much to me.” It’s the perfect song about missing a summer love, dripping with nostalgia with every chord and lyric.
The Police – “Every Breath You Take”
I can’t believe we still need to have this discussion in 2025. But if you’re with your partner and play “Every Breath You Take” on Valentine’s Day, you need to get your ears checked. This isn’t some song about being there for your partner no matter what. It’s the biggest stalker anthem ever written.
It’s not like Sting is trying to hide it either since it sounds like he’s watching someone’s house while singing it. It’s mind-boggling to me how one of the most ominous-sounding songs ever made became so misinterpreted, especially when people have used it as a wedding song. Stay far, far away from this one.
John Mayer – “Heartbreak Warfare”
Fights are one of the worst parts of relationships, especially when there’s a clear disconnect between two lovers. John Mayer explores this beautifully in “Heartbreak Warfare,” the opening track of his 2010 album “Battle Studies.” The lyrics speak of a man in the midst of a communication breakdown with his lover, and he’s trying to hide how much he’s hurting with the line, “Watch my face as I pretend to feel no pain.” But he’s resolved to work through what they’re going through, singing, “I don’t care if we don’t sleep at all tonight, let’s just fix this whole thing now.” For anyone going through a rough stretch with their partner, Mayer reminds you in “Heartbreak Warfare” that there’s still hope even in the darkest moments.