[2026] A Collection of Tear-Jerking Coming-of-Age Songs in Western Music

A Thousand MilesVanessa Carlton

Vanessa Carlton – A Thousand Miles

It conveys the message that one can overcome any hardship to meet the person they deeply care about.

The title “A Thousand Miles” carries the idea: “If I could see you tonight, I would walk a thousand miles to be with you.” Though there is a touch of melancholy, it’s something everyone can relate to.

Story of My LifeOne Direction

One Direction – Story of My Life

One Direction rose from a UK talent show to become a globally beloved group.

Released in October 2013, this track from their third album, Midnight Memories, showcases a mature sound that steps beyond their idol image.

The warm tones of the acoustic guitar, delicate strings, and the layered chorus featuring all the members are breathtaking.

The lyrics, reflecting on time gone by and memories with family, resonate not just as a love song but as a story of life.

The music video features the members’ real families, interweaving childhood photos with the present in a tear-jerking montage.

For those who discovered Western pop through YouTube or MTV, it’s a nostalgic piece that may well overlap with memories of their own youth.

In The StarsBenson Boone

Benson Boone – In The Stars (Official Music Video)

Singer-songwriter Benson Boone from Washington state rose to stardom via TikTok.

Released in April 2022, this work is a tribute ballad that expresses the deep sorrow of losing his beloved great-grandmother through beautiful metaphors of stars and morning scenes.

It begins with a simple, piano-driven accompaniment, and the chorus strikes the heart with soaring high notes.

Later included on the album Fireworks & Rollerblades, it reached the top 10 in countries such as the Netherlands and Norway.

It’s a song that can deeply resonate with middle schoolers grieving the loss of someone precious and grappling with an overwhelming sense of emptiness.

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.

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.

this is what losing someone feels likeJVKE

this is what losing someone feels like (official video)

Jake, a young singer-songwriter who shot to global fame on TikTok, became a familiar name among Japanese music fans after his 2022 hit “golden hour” took the world by storm.

Released in March 2023, this work is a ballad that quietly portrays the regret and pain of losing someone dear.

The protagonist’s feelings—agonizing over small everyday choices like “If only we’d had that coffee together” or “If only I’d picked up the phone”—are poured out over a gentle piano melody.

The delicate emotions of trying to accept the irreversibility of loss may well bring you to tears.

It’s a song that gently stays by your side when you’ve experienced heartbreak or parting.

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.