Love hurts, but unrequited love—for someone who doesn’t share your feelings or for someone who is unavailable—is a particular kind of pain. It’s sadness, regret, frustration, yearning, jealousy all in one painful package. It’s dreaming of what could be and slowly recognizing that you might have missed your moment.Â
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This crucible of heightened emotions has led to best-selling novels, beloved ballets, and chart-topping hits, from soul-baring ballads to rock anthems and everything in between. Here’s a playlist that speaks to all the complicated emotions of unrequited love.
- “If I Could Turn Back Time” – Cher
Where else would you begin a playlist about regret and missed chances than this iconic 1989 anthem from the Goddess of Pop. - “Don’t Make It Harder On Me” – Chloe x Halle
An R&B song about the emotional mess of trying to move on with a new person while having second thoughts about your ex—who wants you back. - “Sorry I’m Here for Someone Else” – Benson Boone
An indie song about that awkward moment when you’re on a date and run into your ex, who you realize you might still love. - “When I Was Your Man” – Bruno Mars
A reflective piano ballad with lyrics that hit you right in the gut. Haunted by his mistakes, the singer regrets letting his pride and ego bring down the relationship. - “If I Knew Then” – Lady A
An introspective song about the consequences of not taking chances and seeing real love for what it is. - “Back to December” – Taylor Swift
With Taylor, there are so many soulful love songs to choose from, but nothing expresses the painful regret over how she treated a past lover quite like this 2010 hit. - “Jessie’s Girl” – Rick Springfield
A rock song about pining after your friend’s girl, like Onegin when he realizes Tatiana is now with someone else. - “What Might Have Been” – Little Texas
A country song exploring all the what ifs of a past relationship that fizzled out. - “It’s Too Late to Love Me Now” – Dolly Parton
Dolly’s incredible voice makes this classic country song about missed chances unforgettable. - “Someone Like You” – Adele
This ballad is both gut-wrenching and empowering, and its cries of regret and heartbreak could apply to both Tatiana and Onegin at different times in the ballet. - “When You Were Mine” – Prince
A new wave song about a messy love triangle and only coming to truly appreciate someone once they are involved with someone else. - “All I Want” – Olivia Rodrigo
In this pop hit from High School Musical: The Musical: The Series, Rodrigo’s character Nini looks back over past relationships and realizes that her fantasies about love aren’t reality. - “Too Little Too Late” – Jojo
A pop song about when your ex finally starts to say what you wanted to hear but you’ve moved on. - “I Want You Back” – Jackson 5
This iconic group’s debut single is about realizing you were too hasty to leave your former relationship. - “I (Who Have Nothing)” – Shirley Bassey
This defiant song in which the speaker is convinced that no one can love this person as much as she does became one of Bassey’s staples; she sang it at most of her live concerts for decades.
