Tear-jerking unrequited love songs that will break your heart: timeless classics about unattainable love
Have you ever had a night when your chest tightens with the weight of feelings that can’t reach the one you love? The power of bittersweet unrequited love songs is that they gently speak the words you can’t say.
The more you think about the person you like, the more the ache grows—and even knowing the love won’t come true, you still can’t stop your feelings.
Finding a song that stays close to such a wavering heart can quietly give you a push after the tears.
In this article, we’ll introduce a wealth of gems that portray the pain of unrequited love with unflinching honesty.
We hope you’ll find the one song that resonates perfectly with how you feel right now.
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Tear-jerking unrequited love songs. Masterpieces about impossible love (101–110)
cherry (sweet cherry; cherry fruit)Otsuka Ai
Ai Otsuka is a singer-songwriter whose energetic charm is irresistible.
The song that catapulted her name into the spotlight is Sakuranbo.
It beautifully captures a girl’s feelings of love, and its lively melody paired with bittersweet lyrics has won great popularity.
La La LaDaikoku Maki
Speaking of Maki Ohguro, she’s a female rock singer who scored numerous hits in the ’90s.
Her husky voice exudes a mature allure.
“La La La” is one of those hits as well, and its chorus—one that makes you want to sing along with everyone—is especially famous.
Baby Sweet Berry LoveOgura Yui
This is the second single by voice actress Yui Ogura, released on May 8, 2013.
It was the ending theme for the TV anime The Hentai Prince and the Stony Cat.
Ogura has also been appointed a tourism ambassador for her hometown, Midori City in Gunma Prefecture.
It’s a very cute love song aimed at hardworking girls.
Falling in LoveKobayashi Akiko
Hearing the name Akiko Kobayashi will likely evoke nostalgia for many older listeners.
Her clear, pure singing voice is remarkably sincere and wonderful.
Her song “Koi ni Ochite – Fall in love” is truly her signature piece and a track that shone in the Showa era.
even ifHirai Ken
This is Ken Hirai’s 11th single, released on December 6, 2000.
Total shipments reached 360,000 copies.
As it was a limited-time release, it is no longer available for purchase.
It’s a song where the lyrics perfectly match Ken Hirai’s vocals.
Tear ducts destroyed by heartbreaking unrequited love songs. Masterpieces that sing of impossible love (111–120)
Fortune Cookie in LoveHirai Ken
Speaking of “Koi Suru Fortune Cookie,” it’s a hit song by AKB48.
This track is a cover of that unrequited-love song by the exceptionally talented vocalist Ken Hirai.
He delivers the originally peppy tune with a mature allure, singing it in a smooth, heartfelt style.
In the Middle of a DreamKisugi Takao
This is a song from Takao Kisugi’s album “Yume no Tochuu,” released on December 10, 1981.
Later, the song was slightly rearranged and provided to Hiroko Yakushimaru.
At that time, the title was changed to “Sailor Suit and Machine Gun.” It’s a song about an adult romance.