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The Meaning Behind The Song: I Know I Shouldn’t by Jack Rootes

The Meaning Behind The Song: I Know I Shouldn’t by Jack Rootes

My Personal Connection to the Song

As a fan of Jack Rootes, his song “I Know I Shouldn’t” has resonated with me on a personal level. The lyrics delve into the complexities of unrequited love and the internal struggle of wanting someone you can’t have. The honesty and vulnerability in this song struck a chord with me, as I have experienced similar emotions in my own life.

The Lyrics

In the first verse, Rootes expresses his conflicting emotions towards someone he has developed strong feelings for. Despite the understanding that pursuing a romantic relationship would be wrong, he can’t help but long for them. There’s a sense of melancholic yearning as he acknowledges their friendship but desires something more.

The chorus highlights Rootes’ internal battle and the choices he could make if he followed his heart’s desires. It’s evident that he understands the consequences of his actions and the pain it could cause others involved. The repetition of “but I know I shouldn’t” emphasizes his internal struggle and his attempt to do what is morally right, even though it’s difficult.

The second verse delves deeper into Rootes’ desire for a meaningful connection with the person in question. He longs for a genuine relationship, rather than a fleeting encounter. However, he acknowledges the barriers that exist, such as her current relationship. Despite the jealousy he feels, Rootes refuses to engage in actions that could jeopardize their happiness.

The song closes with a sense of longing and hope for a future where his feelings might be reciprocated. Rootes acknowledges the possibility of a breakup and the potential for a future together, but remains patient and hopeful.

Analysis and Interpretation

“I Know I Shouldn’t” explores the complexities of unrequited love and the desire for something that appears unattainable. Rootes captures the internal struggle and emotional turmoil faced when feelings are strong but circumstances prevent their fruition. The lyrics reflect the moral dilemmas and self-restraint required when faced with such a situation.

While the song focuses on Rootes’ personal experiences, it also touches on universal themes of longing, temptation, and self-control. It speaks to anyone who has found themselves in a similar predicament, torn between their own desires and doing what is right.

Ultimately, “I Know I Shouldn’t” reminds listeners of the importance of respecting boundaries and considering the feelings of others. It highlights the complexity of human emotions and the challenges we face when our heart pulls us in a different direction.


Jack Rootes’ “I Know I Shouldn’t” is a heartfelt exploration of unrequited love and the struggles that come with it. Through honest and introspective lyrics, Rootes delves into the conflicting emotions and difficult choices faced when longing for someone who is already taken. The song serves as a reminder of the importance of self-restraint and respecting others’ relationships, while also acknowledging the strength of human emotions.

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