[2026] Recommended for junior high schoolers! A roundup of tearjerker Western songs

We Hug NowSydney Rose

Sydney Rose – We Hug Now (Official Video)

Singer-songwriter Sydney Rose, originally from Georgia and now based in Nashville, is an artist known for her whispery vocals and delicate piano and guitar tones.

Released in February 2025, this work portrays not the end of a romance but the breakdown of a friendship.

It quietly narrates the pain of two people who once held each other close but have now become strangers merely passing by.

Vivid scenes linger, like mistaking city lights for stars while remembering the other person, and dreaming of still being seventeen—moving back and forth between past and present.

If you’re a middle schooler struggling with a friendship, be sure to give it a listen.

A COLD PLAYThe Kid LAROI

The Kid LAROI – A COLD PLAY (Official Video)

This track by Australian rapper The Kid Laroi, released in September 2025, is only about two minutes long yet packed with raw feelings of sadness and regret.

Over a cold, minimal beat, he lays bare the reality that you can’t change someone, while conveying the lingering emotions he can’t let go of—a direct transmission of the pain right after a breakup.

Since it came out shortly after his split with ex-girlfriend Tate McRae, it can be seen as a work that strongly reflects his true feelings.

Recommended for middle schoolers who are struggling because they can’t forget someone.

Wish You The BestLewis Capaldi

Lewis Capaldi – Wish You The Best (Official Video)

Lewis Capaldi, known for his chest-tightening piano ballads.

Released in April 2023 as the third single from his album “Broken by Desire to Be Heavenly Sent,” this track is a tearjerker that portrays twisted feelings for an ex.

The protagonist admits that saying they wanted to stay friends was a lie—a confession that will resonate deeply with middle schoolers who’ve experienced heartbreak.

Debuting at No.

1 on the UK charts, the song captivates with an explosive outpouring of emotions that were left unsaid.

If you’re wrestling with complicated feelings of love, be sure to give it a listen.

SKINNYBillie Eilish

Billie Eilish – SKINNY (Official Lyric Video)

This song, which opens the album HIT ME HARD AND SOFT released in May 2024, portrays the protagonist’s complex feelings about being told they “look happy” after losing weight.

It poignantly captures the frustration of being judged based on appearance and the inner conflict of knowing that, despite the outward change, they themselves have not changed.

Billie Eilish’s whisper-like vocals and the beautiful orchestral textures underscore the melancholy of these emotions.

The tension between how society judges people by their looks and one’s true self is a theme that many sensitive middle school students may find relatable.

Wrapped in the dreamy sounds of dream pop, it’s a delicate track that might just bring tears to your eyes.

Good Luck, Babe!Chappell Roan

Chappell Roan – Good Luck, Babe! (Official Lyric Video)

In recent years, singer-songwriter Chappell Roan has been gaining international attention.

She’s won popularity for her expressive artistry rooted in queer culture and a sound reminiscent of 1980s synth-pop.

Released in 2024, this work portrays a relationship with someone who can’t accept their true feelings.

It carries a poignant message to a lover who keeps running from the truth out of fear of society’s gaze: one day, you’ll regret it.

Singing about the struggles of love and the pain of hiding your true self, the song reminds us of the importance of being who we are.

It’s a track I especially hope middle schoolers wrestling with friendship or romance will listen to.

Next SummerDamiano David

Damiano David – Next Summer (Official Video)

Damiano David, the frontman of the Italian rock band Måneskin, enjoys worldwide popularity.

Since 2024 he has been ramping up his solo career, and this track—featured on his album “Funny Little Fears,” released in February 2025—is a pop ballad with a soothing acoustic feel.

On the surface, it sounds like a lament over a summer romance, but it actually carries a deeper message about one’s own fears and anxieties, and the mind’s captivity that keeps us from changing.

The music video, filmed in an Italian prison, visually expresses this theme of an “inner prison,” reinforcing the song’s world and impact.

It’s a song that gently stays by your side when you’re carrying worries you can’t tell anyone about.

How Do I Say GoodbyeDean Lewis

Dean Lewis – How Do I Say Goodbye (Official Video)

Dean Lewis is a singer-songwriter from Australia who has earned international acclaim for his emotionally rich lyrics and deeply resonant melodies.

This track, released in September 2022, was created based on his experience when his father was diagnosed with a serious illness.

The lyrics, which express the fear and love surrounding the inevitability of having to say goodbye to someone precious, offer a deeply relatable reflection on family.

The structure is also superb, unfolding from a quiet piano- and strings-led intro into a gradually intensifying climax.

Check it out when you want to reflect on your relationships with family or revisit your feelings for someone important to you.