How old is too old to listen to songs about failed romance?
When does it become cringe to potently relate to songs about breakups, situationships, and flings?
Some songs are best appreciated after romance gone wrong. This could be a breakup, a situationship or casual fling that dissolved quietly, or having to stop crushing on someone after knowing that the feeling is unrequited.
Maybe it’s listening to Future’s “Throw Away” after learning that an ex has moved on to someone else. Maybe it’s dancing to Kesha’s “Dancing with Tears in My Eyes” or “Harold Song” while you are simultaneously trying to reflect on the tenderness lost with your boo’s exit. Maybe it’s sinking on the sofa to The Strokes’ “Is This It” after getting back from a date knowing that there won’t be a second one. You hear songs like these differently once you have lived through the emotions they describe.
While these songs are incredible on their own, in the context of failed romance, they let you feel sadness, jealousy, lust, resentment, and longing at full intensity. I think it has to do with these feelings being verbalized and solidified for you by these artists; you finally have somewhere to anchor and make sense of them.
My attitude towards such songs have changed slightly as of late, however. I turned twenty-seven last month and also noticed my first grey hairs a couple months back (it runs in the family, though an exceptionally stressful start to 2026 probably didn’t help). With this onset, I have become aware that my body is no longer as spry as it used to be—that I am moving out of youth. What has also followed, as mentioned earlier, is a light embarrassment when listening to songs about missing old flames, yearning for people out of reach, or keeping vulnerability at bay by talking to 2-3 people at the same damn time.
These songs increasingly feel like they belong to youth. Not because people stop falling in love after their twenties, but because the stakes change. When you are young (or younger than twenty-seven), the future seems more open. Every failed relationship feels recoverable because there are always more people to meet, more cities to move to, and more improved—healthier, hotter, and better skilled—versions of yourself waiting around the corner. Rejection hurts, but possibilities soften the blow.
Doors start closing the closer you get to thirty. You know yourself and your limitations better. I know that I will never become someone on the academic, professional, cultural, or physical fitness pantheon. My failed relationships won’t become platinum records. My exes won’t profoundly miss me in a chronic manner; whoever they end up with will probably be my equal, if not better. Not to mention the fact that past thirty, the dating pool starts to shrink exponentially, especially in the Global South. The choppers out of ‘Nam will be in short supply soon and I do not wish to be stranded.
As I feel my age, I no longer feel like identifying with the narrator of the sort of songs I have mentioned so far. I can’t imagine myself pining endlessly for someone who has already moved on. I can’t imagine turning another person into the great, unattainable love of my life when we are both approaching an age where marriage, children, mortgages, and ordinary Tuesday evenings should become more important than romantic mythology. It has become a little difficult to listen to these songs as the protagonist; I now listen to them as someone quietly and slowly aging out of the fantasy they were written for.
This does not mean I will stop listening to them. There is a silver lining to all of this: now that I can stop associating myself with the subjects or objects of these songs, I can appreciate them for their technical aspects better. So if you ever see me bopping to Future at a club, know that I am just feeling his sick flows.