- The probable Trope Namer is an old country standard the Everly Brothers played. Famously Covered Up by Nazareth, who gave it an epic metal treatment. From the sound of the singer's voice, love really hurts.
- Incubus' aptly titled song "Love Hurts", although it could be considered a subversion; the chorus is, "Love hurts, but sometimes it's a good hurt and it feels like I'm alive".
- Another subversion in "Hurt Me Bad (In a Real Good Way)" by Patty Loveless. The protagonist was hurt by love, but the pain set her free to find a better lover.
- Sing with me…Love, love will tear us apart again...
- "... that's the pain that cuts a straight line down through the heart, we call it love ..." - Hedwig and the Angry Inch
- Aerosmith, "Falling in Love (Is Hard On The Knees)".
- "Love Stinks" by The J. Geils Band.
- Baby, don't hurt me... no more... (Haddaway, best known as the theme song for the "Roxbury Guys" on Saturday Night Live.)
- Leonard Cohen's famous "Hallelujah" is mostly about this, although the overall idea seems to be that it's worth it anyway as long as you know what to expect.
- "Running Water" by DJ Shog featuring Irma Derby: "Love's like hot running water, once it runs through your fingers, painful in every way..."
- "Love Bites" by Def Leppard. Describes love as an addiction.
- "Love Is For Suckers" by Twisted Sister.
- Half the Rumours album by Fleetwood Mac are songs about how bitter falling out of love can be. "Never Going Back Again," "Go Your Own Way," and "Gold Dust Woman" in particular. The crowner is "The Chain," an anger-filled tune ("Damn your love, damn your lies") and is the only song on the album credited to all five members.
- XTC's "I'm the Man Who Murdered Love" depicts the title character as a highly Sympathetic Murderer.
- "To Love Somebody", originally by The Bee Gees.
- "It's a Heartache", originally by Bonnie Tyler (and Juice Newton).
- "Too Much Love Will Kill You" by Brian May.
- "Fool for Your Loving" by Whitesnake.
- "Only Love Can Hurt Like This" by Paloma Faith.
- "Lollipop" by Mika.
Mama told me what I should know:"Too much candy gonna rot your soulIf she loves you, let her go'Cause love only gets you down"
- "Adult Female: A Song" by Hank Green
"Love is hard and love is messy and it can hurt worse than fire
and sometimes it makes you want to tear down a building with your bare hands!"
- The song "You Always Hurt The One You Love".
"You always hurt the one you love/The one you shouldn't hurt at all"
- "Terrible Thing" by Mayday Parade, which is song from the viewpoint of a father telling his son about how he met, fell in love with and married his mother. It then reveals the mother in fact died years ago and the father than tells his son that he should never fall in love and avoid anyone that tries to make him do so, because life can do terrible things.
- "Breaking Us In Two" by Joe Jackson is about a couple who love each other but just can't make the relationship work long-term.
- Daniel Johnston lives this trope. He has been in love with many girls, but due to his mental illness all of it has remained Unrequited Love, resulting in a lot of very tragic but heartfelt songs, including on his albums Yip/Jump Music and Hi, How Are You.
- Billie Holiday had a tragic life where she was the victim of rape at age 11, teenage prostitution, abusive partners and severe alcohol, morfine and heroin addiction. All it culminated in Lady in Satin, where she sings about break-ups, unrequited love and all hardships of relationships in her drug ravaged voice. Only a year after recording this album she would die from liver cirrosis.
- Garbage's "I Hate Love", a long diatribe on the ways it hurts - specially not being loved back.
- "Everything We Had" by The Academy Is... "Take the pain out of love, and then love won't exist..."
- Taking Back Sunday's 'Bonus Mosh Pt. 2' - "It's love, make it hurt."
- "Stigmata of Love" by Magic Affair likens the pain of love to the wounds of the crucified Jesus Christ.