In Ari Hest's song "When To Quit," the lyrics depict a tale of heartbreak and the struggle to let go of a past love. The protagonist finds themselves in a dark and difficult place, trying to come to terms with the end of their relationship. The opening lines, "Here in the dark, I'm getting my fill, my climb back up appears one menacing hill," convey the feeling of being overwhelmed and uncertain about how to move on. The protagonist questions their ability to find the strength and willpower to try again. As the song progresses, the lyrics mention the memories and moments shared with their former partner. They unravel the boxes holding the remnants of their past love and let go of their connection by lowering the mast and signaling the end. However, the emotions rush in like charging waves, leaving them unsure if they made the right decision. They wonder if this separation is truly meant to be. The chorus, "I don't want to break your heart any more than it's been broken, it was enough for you the veil I knit, but I didn't know when to quit," reveals the protagonist's guilt and remorse for hurting their partner. They acknowledge that they have already caused pain and wish not to inflict any further damage. They realize that they held on for too long, unable to let go. The lyrics also showcase the protagonist's struggle to move on. They hold onto innocent memories of their partner, feeling their presence as an everlasting embrace. While loved ones reassure them that time will heal, the protagonist remains afraid and uncertain, knowing they have caused harm. In the final part of the song, the protagonist contemplates their feelings for their former partner and the possibility of a reconciliation. They admit that thinking of their ex brings a smile, but they are still unconvinced if they are truly meant to be together. Overall, "When To Quit" portrays the internal turmoil and confusion one experiences when trying to navigate the end of a relationship. It delves into themes of regret, doubt, and the difficulty of letting go, ultimately offering a glimpse into the complexities of human emotions.