Whether you love it, hate it or tout it as a Hallmark holiday, there’s no denying Valentine’s Day can make even the most content of single people think a little more wistfully about romantic date nights. While I usually spend the holiday curating the perfect romantic comedy double feature to watch alone while cozy in bed, this year I’m feeling a little cynical.

Maybe it’s the stress of midterms, maybe it’s because I can’t catch the annual Music Box Theatre screening of “The Princess Bride” because of my conflicting night class schedule. Either way, my playlist for the holiday is relishing in the misfortune of other people’s breakups. Meaning, what if I just made a playlist of love songs about couples that would eventually split up? Love may not be real but I’ll be damned if the soundtrack doesn’t at least slap.

“Love is a Laserquest” by Arctic Monkeys

My Roman Empire is the love letter Arctic Monkeys’ frontman Alex Turner wrote for model and internet personality Alexa Chung. No, I don’t care if that Internet meme is over. The love letter is so heart-shattering that it still lives in my mind rent-free. While the singer’s four-year relationship with the iconic Tumblr it-girl may have resulted in their 2011 breakup, it also produced my favorite album of all time, “Suck It And See.” If any hot guy in a band wants to write a love song about me, please know the bar is high purely because of this song. 

“Until I Found You” by Stephen Sanchez

Although this song may now be better known as a viral Tiktok sound, “Until I Found You” was once just a love song for Stephen Sanchez’s high school girlfriend Georgia Webster. Although it’s unclear when exactly the pair dated and broke up, Webster is actually featured on the song in backup vocals. “Until I Found You” was later turned into a duet with Sanchez and singer Em Beihold, both of whom are signed to Republic Records. The moral of the story is: even if you do break up with your rockstar boyfriend, make sure he’s forced to sing about you — and consequently think about you — at every concert for the rest of his career.  

“If Not For You” by Måneskin

Before Damiano David made his red carpet debut with Dove Cameron at this year’s Pre-Grammys Gala, he was in a long-term relationship with Italian model Giorgia Soleri. “If Not For You” is one of the best ballads on Måneskin’s album “Rush” and while I can’t confirm this song is actually about their relationship, the timeline does technically work. The album this song is featured on was released in January 2023 while David and Soleri only broke up in June 2023. Meaning, because they were still together when this song was written, produced and released, I’m going to convince myself it’s about Soleri — mainly for the sake of this DeJamz theme. 

“Pumpkin” by The Regrettes

You know that one song every girl posts on their Instagram story the second the leaves turn orange in autumn? This is it. “Pumpkin” is a swoon-worthy love ballad dedicated to lead singer Lydia Night’s then-boyfriend Dylan Minnette. A mellow bass, lulling vocals and subtle pop-genre edge craft an indie song that makes you want to slow dance in the kitchen with that someone special. The pair split in late 2022 after four years together but this song remains as a longing reminder of what was. Even The Regrettes split up in December 2023, so maybe all types of love, romantic or platonic, are dead.