20 Songs About Complicated Love

Love is a beautiful, yet often complicated emotion. It can bring us immense joy and fulfillment, but it can also lead to heartbreak, confusion, and frustration. As someone who has experienced the ups and downs of complicated love firsthand, I know how challenging it can be to navigate the twists and turns of a relationship that is anything but simple.

In this playlist, I’ve compiled a list of 20 songs that perfectly capture the essence of complicated love. From the euphoria of falling head over heels to the agony of a broken heart, these songs speak to the universal experiences we all face when love becomes a tangled web of emotions.

1. “One Thousand Times” by James Vincent McMorrow

James Vincent McMorrow’s “One Thousand Times” delves into the complexities of love and regret. The song’s protagonist grapples with the pain of losing love and the desire to reclaim it. The lyrics express a deep yearning and a sense of loss, encapsulating the emotional turmoil that comes with complicated relationships. McMorrow’s haunting vocals and the melancholic melody enhance the song’s introspective and sorrowful tone. The repetition of the phrase “I don’t want to live without your love” underscores the desperation and the cyclical nature of longing and heartache.

2. “Sand In My Shoes” by Dido

“Sand In My Shoes” by Dido narrates a bittersweet tale of a fleeting romantic encounter during a holiday. The song captures the wistfulness of returning to everyday life while reminiscing about a brief, yet impactful, romance. Dido’s lyrics reflect the tension between the joy of the memory and the sadness of its impermanence. The metaphor of sand in her shoes symbolizes the lingering presence of the past experience, even as she moves forward. The song’s upbeat tempo contrasts with its reflective lyrics, creating a poignant depiction of love’s transient nature.

3. “I Wanna Die” by Miranda Lambert

Miranda Lambert’s “I Wanna Die” is a raw and candid exploration of a tumultuous relationship. The song portrays the emotional highs and lows of love, where passion and pain are intertwined. Lambert sings about the paradox of loving someone who causes immense hurt, yet being unable to let go. The lyrics highlight the contradictions and complexities of such relationships, where love and hate coexist. The recurring line “If you’re the death of me, darling, I wanna die” encapsulates the intensity and the self-destructive tendencies that can accompany complicated love.

4. “Does Anyone Know” by Scorpions

“Does Anyone Know” by Scorpions addresses the confusion and disillusionment that often accompany love. The song’s protagonist questions the authenticity and stability of their relationship, expressing doubts and a sense of loss. The lyrics convey a struggle to understand the shifting dynamics of love and the difficulty in finding truth and trust. The chorus, “Does anyone know the truth we’re looking for, can’t find it anymore,” reflects a deep sense of uncertainty and a longing for clarity. The song’s rock ballad style amplifies the emotional weight of its themes.

5. “U” by Kendrick Lamar

Kendrick Lamar’s “U” is a deeply introspective track from his album To Pimp a Butterfly. The song explores themes of self-hatred, depression, and survivor’s guilt. Lamar uses the song to confront his inner demons and the pressures he faces from his environment and his own expectations. The repeated line “loving you is complicated” is directed towards himself, highlighting his internal struggle and the complexity of self-love amidst external and internal turmoil. The song’s raw emotion and candid lyrics make it a powerful commentary on the difficulties of maintaining one’s mental health and self-worth in the face of adversity.

6. “Complicated” by Tanya Tucker

Tanya Tucker’s “Complicated” is a country song that delves into the intricacies of love and relationships. The lyrics reflect the emotional rollercoaster of being in a relationship where feelings are tangled and often contradictory. The song portrays a sense of longing and confusion, as the protagonist navigates the ups and downs of love. Tucker’s emotive delivery and the song’s poignant melody underscore the bittersweet nature of complicated love, making it a relatable anthem for anyone who has experienced the complexities of romantic relationships.

7. “P.S. (I’m Still Not Over You)” by Rihanna

“P.S. (I’m Still Not Over You)” by Rihanna is a heartfelt ballad from her album A Girl like Me. The song captures the lingering feelings of love and regret after a breakup. Rihanna’s lyrics express a deep sense of longing and unresolved emotions, as she confesses that she is still not over her ex. The song’s reflective tone and emotive delivery highlight the pain of moving on from a past relationship, making it a poignant exploration of the enduring impact of love.

8. “Complicated” by Fitz and the Tantrums

“Complicated” by Fitz and the Tantrums is an energetic track that delves into the tumultuous nature of a passionate yet unstable relationship. The song describes the push-and-pull dynamic between two people who are drawn to each other despite the chaos they create together. The lyrics depict a cycle of intense physical attraction and emotional conflict, encapsulated in the chorus “It’s complicated when we get naked, but I can take it.” The upbeat tempo and catchy melody contrast with the song’s theme of complicated love, highlighting the paradoxical nature of such relationships.

9. “Feels So Right” by Janet Jackson

“Feels So Right” by Janet Jackson is a celebration of enduring love that faces challenges but remains strong. The song expresses a deep connection between two people who believe that their love can overcome any obstacle. The lyrics convey a sense of gratitude and commitment, with Jackson singing about the strength and resilience of their bond. Despite the positive tone, the underlying message acknowledges that maintaining such a relationship requires effort and perseverance, highlighting the complexities of love that feels right but demands work to sustain.

10. “Take Your Hand” by Usher

Usher’s “Take Your Hand” from his album Confessions deals with the inner conflict and confusion that arise in a complicated relationship. The song describes the protagonist’s struggle with intense emotions and doubts about whether to continue the relationship or let go. Usher’s lyrics capture the push-and-pull dynamic, where the attraction is strong, but so are the uncertainties. The chorus, “Do I take your hand or let go?” encapsulates the indecision and emotional turmoil that often accompany complicated love. The song’s soulful melody and Usher’s expressive vocals add depth to the portrayal of this emotional struggle.

11. “Woman Don’t Want to Love Me” by Chicago

“Woman Don’t Want to Love Me” by Chicago, from their album Chicago VII, explores the pain and frustration of unreciprocated love. The song’s protagonist laments that his partner no longer wants to love him, citing various reasons such as feeling low and wanting to leave. The lyrics emphasize that love is complicated and requires effort and commitment, which the woman is no longer willing to give. The song’s funky rhythm and powerful horn sections contrast with the somber theme, creating a dynamic portrayal of the complexities and heartbreak of a failing relationship.

12. “Confused” by Lenny Kravitz

“Confused” by Lenny Kravitz is a rock song that delves into the bewildering nature of love and relationships. The lyrics describe the protagonist’s inability to understand and navigate the emotional landscape of a romantic relationship. Kravitz sings about the challenges of getting things right between a man and a woman, highlighting the misunderstandings and mixed signals that often occur. The song’s energetic guitar riffs and Kravitz’s passionate delivery underscore the frustration and confusion that come with trying to make sense of love’s complexities.

13. “Complicated” by Avril Lavigne

“Complicated” by Avril Lavigne is a quintessential song about the frustrations of dealing with someone who acts differently in public compared to when they are alone. The song’s lyrics express the protagonist’s irritation with their partner’s tendency to put on a facade, highlighting the complexities and challenges of maintaining authenticity in relationships. Lavigne’s pop-punk style and candid lyrics resonated with many, making it a relatable anthem for those who have experienced similar frustrations. The song’s success, peaking at number two on the Billboard Hot 100 and earning two Grammy nominations, underscores its widespread appeal and impact.

14. “Start Again” by Counting Crows

“Start Again” by Counting Crows is a reflective song that delves into the desire to reset and rebuild a relationship that has faced numerous challenges. The lyrics convey a sense of regret and longing for a fresh start, acknowledging the mistakes and misunderstandings that have complicated the relationship. The song’s melancholic melody and introspective lyrics capture the emotional weight of wanting to mend a fractured bond. The recurring theme of starting over highlights the complexities of love and the hope for redemption and renewal.

15. “It Should Be Easy” by Britney Spears

“It Should Be Easy” by Britney Spears, featuring will.i.am, explores the paradox of love that should be straightforward but is fraught with complications. The song’s lyrics express frustration over the disconnect between the ideal of effortless love and the reality of its challenges. Spears and will.i.am sing about the difficulties of maintaining a relationship despite their strong feelings for each other. The upbeat tempo and electronic production contrast with the song’s theme, emphasizing the irony of love that is anything but easy.

16. “Confused In Love” by Keyshia Cole

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“Confused In Love” by Keyshia Cole is an emotional ballad that delves into the turmoil of being in a relationship where feelings are mixed and uncertain. The lyrics describe the protagonist’s struggle with conflicting emotions, feeling both love and confusion towards their partner. Cole’s powerful vocals and the song’s soulful melody amplify the emotional intensity, capturing the heartache and bewilderment that come with complicated love. The song resonates with anyone who has experienced the uncertainty and emotional conflict of a tumultuous relationship.

17. “Complicated” by Rihanna

Rihanna’s “Complicated,” from her album Loud, explores the frustrations and emotional turmoil of being in a relationship with someone who is difficult to love. The lyrics express the protagonist’s struggle with understanding and connecting with their partner, who makes the relationship unnecessarily challenging. The refrain “You’re not easy to love” highlights the central theme of the song—navigating the complexities of a love that feels more difficult than it should be. Rihanna’s powerful vocals and the song’s dance-pop production underscore the emotional intensity and exasperation of dealing with a complicated partner.

18. “Simple Things” by Usher

“Simple Things” by Usher reflects on the importance of appreciating the fundamental aspects of love and relationships, rather than getting caught up in materialistic or superficial concerns. The song’s lyrics emphasize the value of genuine connection and the simple pleasures that come from being with someone you truly care about. Usher’s smooth vocals and the song’s soulful melody convey a sense of sincerity and warmth, highlighting the contrast between the simplicity of true love and the complications that often arise from external pressures and expectations.

19. “Complicated Disaster” by Tina Turner

Tina Turner’s “Complicated Disaster” delves into the chaos and turmoil of a relationship fraught with deceit and hidden truths. The song tells the story of a partner living a double life, creating a web of lies that ultimately leads to emotional destruction. Turner’s powerful voice and the song’s rock-infused sound capture the intensity and drama of the situation. The lyrics paint a vivid picture of betrayal and the unraveling of trust, illustrating the devastating impact of a relationship that becomes a “complicated disaster”.

20. “Hurts So Good” by Astrid S

“Hurts So Good” by Astrid S explores the paradoxical nature of a relationship that is both painful and irresistibly alluring. The song describes a dynamic where the emotional highs and lows are so intense that the pain becomes an integral part of the attraction. The lyrics convey the struggle of being drawn to someone despite knowing the relationship is toxic. Astrid S uses vivid metaphors and a catchy pop melody to capture the bittersweet essence of a love that “hurts so good,” highlighting the addictive cycle of pleasure and pain.

Submit Your Song to This Playlist

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Serena Whitfield

Serena Whitfield is the founder of PlaylistCurator.org. She’s a musician who writes songs for bands. She studied music at the University of Oxford and graduated with distinction. With her expertise, she knows how to review songs and understand what makes good and bad music. Every playlist on our platform is approved by her before publishing to maintain top-notch quality. If you want her to check out your song and maybe get featured on our playlist, submit your song for Serena to evaluate.