5 Songs That Describe Our Universally Awkward Phases

Whether you were an earlier bird or late bloomer, no kid can escape the uncomfortable time around puberty. Luckily, we can look back in fondness with songs that bring up all the cringey memories.

Written by Gracie Warhurst

Neo-folk artist Briston Maroney asked fans on his Twitter for submissions of their “cringiest middle school pics” to use as the background for the lyric video for “It’s Still Cool If You Don’t.” The song embodies the feelings you’d have for your first crush: wanting to talk to them, not knowing what to say, and regretting ever calling them in the first place. Although sometimes painful, these ‘firsts’ are part of the human experience, and it’s comforting to remember that we all felt that way at one time or another. Thus come the songs that instill a certain cringe-inducing nostalgia of our tween and teen days.

“Teenage Dirtbag” — Wheatus

Similar to “It’s Still Cool If You Don’t,” “Teenage Dirtbag” talks about a seemingly unrequited crush in high school. The narrator, a self-proclaimed undesirable nerd, compares himself to his crush’s boyfriend, listing all the ways he doesn’t measure up. However, just when he thinks all hope is lost and attends prom alone, she walks up to him with tickets to his favorite band.

Wheatus pinpoints the adolescent fear of being ‘uncool,’ comparing yourself to anyone you deem more attractive or popular, and the fantasy of your crush choosing you anyways, using the lyrics “How does she know who I am? / And why does she give a damn about me?” Our narrator does seem to have a bit of a ‘not like other boys’ mentality (he listens to Iron Maiden!), but if we’re being honest, who hasn’t had their YA novel main character moment? This 2000s hit checks every box of a wallflower’s school experience.

“Sadie Hawkins Dance” — Relient K

“Sadie Hawkins Dance” is another school dance song — except this time, Relient K’s Matt Thiessan sings about the anticipation of eventually being asked, not of the fear of going stag. The high school boy goes the whole day listening in on the girls’ conversations, unable to focus on his classes, and is fixated on his own clothing. He’s more of a class clown and narrowly escapes a bully who threatens him for his antics. In the end, the girl admires his wit, and he scores himself a date to Sadie Hawkins.

This sort of overstated confidence is just the alternate side of the coin from “Teenage Dirtbag” and the awkward times in our lives. The band sings, “Then told a funny joke / And the whole class laughing / Think I got a tan from the light in which I was baskin'.” Overcompensating with jokes, second guessing fashion choices, and being overall quite cocky masks insecurity just as much as it exudes confidence. Relient K hit the nail on the head with this picture of the goofy kid pining for a date.

“Awkward” — Tyler, The Creator

If there was only one song to sum up the painstaking anticipation during a first date, kiss, or relationship, it would be this one. Tyler, The Creator raps and sings about being a scrawny 16 year old and going out with a girl. They are out later than they should be and are moments from their first kiss. He hits the high points of feeling the onset of first love, singing, “Man this feels like a dream because our lips locked,” and then the disappointment and embarrassment when it doesn’t quite work out with the lyrics, “Wait, don't think this is going to work / Things got complicated and a couple feelings got hurt.”

This is the most realistic depiction of a first kiss out there: staring at each other awkwardly until one of you makes the first move and turning that one moment over and over in your head. The repetitive nature of this song is quite fitting, mimicking the one-track mind of teenagers when it comes to relationships. There’s also an added element of exploring one’s sexuality ever since Tyler, The Creator came out as queer. He sings, “Gentleman I was like I wasn't trying to f-ck / But it was my first official date so I was stuck like.” In this song, he speaks about a heterosexual relationship which ultimately doesn’t work out, but it paved the way for his first experience regardless.

“Your Graduation” — Modern Baseball

In a slight change of focus, “Your Graduation” appeals more to the tail end of those awkward phases, centering around letting go of someone who doesn’t treat you right. Although Jake Ewald sings about a lost romantic interest, his lyrics can also apply to friendships with the lines, “Bullshit you f-cking miss me / There, I said it, I guess I'll talk to you in a few months,” echoing the pride of not reconciling after a fight even when you miss them. He describes pining after this person, getting drunk to deal with them, staying up all night thinking about the situation, and eventually giving up all together.

“Your Graduation” encapsulates a more tragic aspect of being a teenager — sometimes relationships just aren’t meant to be no matter how hard you try. Modern Baseball pulled together loss, aggravation, and that sort of ‘f-ck you’ mentality that can develop in any young adult after enough time. Their angsty, alternative sound wraps up these feelings nicely to deliver their message.

“4EVER” — Clairo

In “4EVER,” Clairo muses internally about the conflict of being stuck in life while also changing as a person. She asks herself if her feelings will ever change as her friend asks her why she looks so different, prompting Clairo to wonder if her friend will have any part in her future.

While simple, Clairo’s lyrics are relatable, especially during the natural transitions in life. She sings, “Or why I don't look the same / Why are things so differently now?” — a question young people might ask themselves often. Adolescents go from middle school to high school to college without much say in the matter. These experiences change the way young adults present themselves and sometimes the friends or people they associate with, but some feelings can seem never-ending. “4EVER” touches not only on the different rites of passage in adolescence but also the problems that can persist as we navigate through each of them.

Despite the fact that we actually have to live through uncomfortable moments, these songs can help us feel a little less alone. And since no one can escape growing up, at least we can keep playing the soundtrack to our lives.