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

It’ll Be OkayShawn Mendes

Shawn Mendes – It’ll Be Okay

A piano ballad released in December 2021.

Canadian singer-songwriter Shawn Mendes delivers a quiet portrayal of the pain and acceptance of facing a breakup.

It begins by questioning the end of a relationship, then offers a vow to keep loving the other person—a message that resonates, wrapped in organ-like synths and strings.

When you’ve parted ways with someone important, whether in friendship or romance, there are moments when you want to tell yourself, “It’s going to be okay.” This song gently stays by your side in those moments.

The music video, set against nighttime views of his hometown Toronto and snowy scenes, leaves a strong impression with its world that balances loneliness and warmth.

Recommended for those going through heartbreak, as well as middle schoolers struggling with a relationship.

Flightless Bird, American MouthIron&Wine

Iron & Wine – Flightless Bird, American Mouth [LIVE VIDEO]

A track by American singer-songwriter Iron & Wine.

Released in 2007, it reached No.

2 on the U.S.

charts and is included on his third album, The Shepherd’s Dog.

The track was used in the film Twilight.

BAD FEELINGSBLÜ EYES

BLÜ EYES – BAD FEELINGS (Official Music Video)

This song carefully portrays the pain of suppressing emotions and the inner turmoil of feeling pressured to stay positive.

Katie Stamp, also known as Blue Eyes, is a singer-songwriter gaining attention in the indie pop scene, and she released the album “The Last Songs I’ll Write About You” in May 2023.

This piece was released in August 2025 and was created from the perspective of what she would tell her 10-year-old self about emotions.

It teaches the importance of truly feeling your feelings instead of forcing a smile when you’re sad.

If you’re a middle schooler struggling with friendships or your future, be sure to check out the Japanese translation as well.

I Love You, I’m SorryGracie Abrams

Gracie Abrams – I Love You, I’m Sorry (Official Music Video)

A quietly sung piece about the lingering feelings for that person we loved but broke up with—something everyone runs into sooner or later.

Gracie Abrams is a rising singer-songwriter known for opening on Taylor Swift’s tour, and this track, included on her second album The Secret of Us released in June 2024, became a global hit in no time.

The lyrics confess a contradictory feeling—“I love you, I’m sorry”—as she recognizes both the trouble she caused and her own weakness in being unable to let go.

It’s a portrait of complex emotions that many can relate to.

Whispered vocals over gentle guitar and piano tones tenderly embrace the pain deep in the heart.

For those who can’t recover from heartbreak or who haven’t sorted out their feelings for an ex, this song is sure to be one that stays close to you.

teenage dreamOlivia Rodrigo

Olivia Rodrigo – teenage dream (Official Lyric Video)

For middle schoolers who feel anxious that “I should be growing up already, but maybe the best part of me is already gone,” I’d like to recommend this track from Olivia Rodrigo’s second album, GUTS.

Released in September 2023, it’s an introspective piano ballad she wrote just before turning 19, after years of being told she was “mature for her age.” It quietly sings of the hopes and fears of growing up, and the guilt of not becoming your ideal self, offering deep comfort to students who feel rushed or worried about the future.

SamsonRegina Spektor

Regina Spektor – “Samson” [OFFICIAL VIDEO]

A track inspired by a biblical episode.

It sings about love.

Released by American singer-songwriter Regina Spektor, it became a hit in countries such as Belgium, Sweden, Australia, and the United Kingdom.

Hide And SeekImogen Heap

Imogen Heap – Hide And Seek (Official Video)

A track that sings about the unfairness of life.

It was released in 2005 by the British singer-songwriter Imogen Heap.

It was inspired by her experience of her parents’ divorce when she was 12.

The track has been certified Gold in the United States.