13 Best Taylor Swift Songs About Unrequited Love, Ranked (2023)

Ah, unrequited love – that heart-wrenching feeling we’ve all experienced at least once in our lives. And who better to put those emotions into words than our very own pop princess, Taylor Swift.

She has the uncanny ability to write tunes that sound like personal diary entries, catapulting her into stardom and into our hearts. In this compilation, we delve into the depths of T-Swizzle’s oeuvre to bring you the most poignant songs of one-sided affection.

Buckle up and grab some tissues as we count down the best Taylor Swift songs about unrequited love!

Related: Taylor Swift Songs Not About Love | Taylor Swift Christmas Songs | Saddest Taylor Swift Songs | Taylor Swift Love Songs

1. “Teardrops On My Guitar” (2006)

🎵 Song Name: Teardrops On My Guitar
🧑 Artist: Taylor Swift
💿 Album: Taylor Swift
📅 Release Date: 2006
🕒 Song Duration: 3 minutes 23 seconds

“Teardrops On My Guitar” from Taylor Swift is a heartfelt song about unrequited love. In this 2006 hit, Taylor Swift shares her pain of being infatuated with someone who doesn’t notice her feelings.

The poignant lyrics, such as “I fake a smile, so he won’t see”, resonate with listeners who have experienced similar emotions. The song showcases Swift’s talent in crafting relatable songs and is a standout in her discography as a genuine portrayal of unreciprocated love.

2. “invisible string” (2020)

🎵 Song Name: invisible string
🧑 Artist: Taylor Swift
💿 Album: folklore
📅 Release Date: 2020
🕒 Song Duration: 4 minutes 13 seconds

“invisible string” from Taylor Swift’s album folklore is a heartfelt reflection on fate and love. The song’s lyrics illustrate how various life events and colors, like green grass in Centennial Park, connect two people through an “invisible string.” Swift’s vulnerable storytelling highlights the idea of unrequited love and its transformation into a destined connection.

This tender song resonates with listeners, making it one of Swift’s best tracks about love.

3. “You Belong With Me” (2008)

🎵 Song Name: You Belong With Me
🧑 Artist: Taylor Swift
💿 Album: Fearless (Big Machine Radio Release Special)
📅 Release Date: 2008
🕒 Song Duration: 3 minutes 52 seconds

In “You Belong With Me” from Fearless (Big Machine Radio Release Special), Taylor Swift expresses unrequited love while showcasing her relatable storytelling skills. The lyrics paint a picture of a girl secretly in love, pining for her best friend who’s dating someone incompatible.

The song resonates with listeners experiencing similar situations, with its catchy melody and strong themes of friendship and longing. The line “She wears high heels, I wear sneakers” highlights the contrast, making it a memorable anthem for unrequited lovers.

4. “gold rush” (2020)

🎵 Song Name: gold rush
🧑 Artist: Taylor Swift
💿 Album: evermore
📅 Release Date: 2020
🕒 Song Duration: 3 minutes 5 seconds

“Gold Rush” from Taylor Swift’s 2020 album evermore is a captivating take on unrequited love. Swift’s poetic lyrics paint a picture of idealized beauty while highlighting the bittersweet truth of unattainable romance.

Lines like “I don’t like that falling feels like flying ’til the bone crush” perfectly depict the torturous nature of falling for someone out of reach. “Gold Rush” leaves listeners marvelling at its haunting melody and exploring the raw emotions of unfulfilled desires.

5. “Hey Stephen” (2008)

🎵 Song Name: Hey Stephen
🧑 Artist: Taylor Swift
💿 Album: Fearless (Platinum Edition)
📅 Release Date: 2008
🕒 Song Duration: 4 minutes 14 seconds

“Hey Stephen” from Taylor Swift’s 2008 album Fearless (Platinum Edition) is a charming tune about unrequited love. The catchy lyrics convey the excitement and vulnerability of falling for someone, as Swift expresses her feelings to Stephen, boldly asking him to notice her.

This relatable anthem resonates with listeners experiencing their own “Stephen” in life, making it one of the best Taylor Swift songs capturing the essence of a seemingly hopeless crush.

6. “Red” (2021)

🎵 Song Name: Red
🧑 Artist: Taylor Swift
💿 Album: Red (Taylor’s Version)
📅 Release Date: 2021
🕒 Song Duration: 3 minutes 43 seconds

“Red” from the album Red (Taylor’s Version) is a captivating and emotional song by Taylor Swift about unrequited love. The vivid imagery of “driving a new Maserati down a dead-end street” and “colors in autumn” conveys the intensity and fleeting nature of passion.

Delving into heartbreak, lyrics like “losing him was blue” and “missing him was dark gray” capture the complex emotions of a relationship’s end. “Red” remains a standout Taylor Swift song that tugs at listeners’ heartstrings.

7. “ivy” (2020)

🎵 Song Name: ivy
🧑 Artist: Taylor Swift
💿 Album: evermore
📅 Release Date: 2020
🕒 Song Duration: 4 minutes 20 seconds

In “ivy” from Taylor Swift’s album evermore, Taylor explores a captivating narrative of unrequited love and longing amidst an alluring, ivy-covered setting. Masterfully, she expresses the agony of being caught in an emotional tangle of love and betrayal.

Her lyrics delve deep into the uncertain dynamics of an extramarital affair. Listeners are captivated by the beautifully haunting imagery and the raw emotions pouring through each verse, leaving a powerful impact.

8. “illicit affairs” (2020)

🎵 Song Name: illicit affairs
🧑 Artist: Taylor Swift
💿 Album: folklore
📅 Release Date: 2020
🕒 Song Duration: 3 minutes 11 seconds

In “illicit affairs” from Taylor Swift’s 2020 album folklore, she explores the emotional struggles of unrequited love within a secret relationship. The lyrics depict the pain and secrecy of affairs, ultimately leading to self-destruction.

Swift’s poignant storytelling captivates listeners, as she illustrates the constant lies and deceit involved in these situations. “illicit affairs” serves as a powerful reminder of the heartbreaking consequences that can arise from unrequited love.

9. “‘tis the damn season” (2020)

🎵 Song Name: ‘tis the damn season
🧑 Artist: Taylor Swift
💿 Album: evermore
📅 Release Date: 2020
🕒 Song Duration: 3 minutes 50 seconds

The song “’tis the damn season” by Taylor Swift from the 2020 album evermore is a captivating homage to unrequited love. The lyrics depict a fleeting romance enveloped in the nostalgia of returning home.

Taylor skillfully weaves a story of confronting past feelings and what-ifs, evoking strong emotions. With its powerful blend of relatability, tenderness, and longing, “’tis the damn season” easily becomes one of her standout tracks about unrequited love.

10. “tolerate it” (2020)

🎵 Song Name: tolerate it
🧑 Artist: Taylor Swift
💿 Album: evermore
📅 Release Date: 2020
🕒 Song Duration: 4 minutes 5 seconds

“tolerate it” from Taylor Swift’s breathtaking album evermore showcases an emotionally charged story of unrequited love. With poignant lyrics, Swift paints the picture of a relationship where her affection isn’t truly appreciated.

Delicate vulnerability laced with heartbreaking imagery like “I wait by the door like I’m just a kid,” drives home the feeling of giving everything while receiving nothing. This gripping track solidifies “tolerate it” as one of Swift’s most powerful songs about unrequited love.

11. “august” (2020)

🎵 Song Name: august
🧑 Artist: Taylor Swift
💿 Album: folklore
📅 Release Date: 2020
🕒 Song Duration: 4 minutes 22 seconds

“august” by Taylor Swift from her 2020 album folklore is a poignant song of unrequited love. The lyrics reminisce on a summer romance that slipped away, with lines like “August sipped away like a bottle of wine.” The bittersweet track resonates with listeners as it highlights the pain of yearning for a love that was never truly theirs.

“august” stands out among Swift’s discography as an emotional and honest portrayal of heartache.

12. “Enchanted” (2010)

🎵 Song Name: Enchanted
🧑 Artist: Taylor Swift
💿 Album: Speak Now
📅 Release Date: 2010
🕒 Song Duration: 5 minutes 52 seconds

“Enchanted” from Taylor Swift’s 2010 album, Speak Now, beautifully captures the essence of unrequited love. The lyrics evoke a sense of longing, hinting at a magical meeting between two strangers.

The song’s impact lies in the powerful emotions we’ve all felt—wondering if the other person feels the same connection. Swift’s heartfelt performance cements “Enchanted” as one of the best songs about unrequited love in her repertoire, making listeners feel both wonderstruck and hopeful.

13. “Cruel Summer” (2019)

🎵 Song Name: Cruel Summer
🧑 Artist: Taylor Swift
💿 Album: Lover
📅 Release Date: 2019
🕒 Song Duration: 2 minutes 58 seconds

“Cruel Summer” from Taylor Swift’s 2019 album Lover is a perfect example of a song with unrequited love theme. The lyrics portray a forbidden summer romance, filled with passion and longing.

Lines like “killing me slow, out the window” and “what doesn’t kill me makes me want you more” highlight the intense feelings she experiences. The song’s catchy melody and relatable emotions caused a significant impact on listeners, making it a standout track in Taylor’s discography.