The song "Ashamed" by Jamestown Story explores the emotions of feeling lost, regretful, and trapped in a cycle of self-destructive behavior. The lyrics suggest a sense of not knowing what is right or wrong and the consequences of one's actions. The protagonist admits to wasting their efforts in trying to move on from their mistakes and takes responsibility for the choices they have made, expressing that they have no excuse for their behavior. The song acknowledges feelings of shame and the burdens that come with it, but also emphasizes that the person they are addressing is the reason they continue to persevere. This could imply that the love or support from someone else is what gives them hope and drives them to keep going despite their shame. The lyrics also touch upon the singer's uncertainty about how they ended up in their current situation, admitting to not knowing where they went wrong. They describe themselves as an aging player who can't seem to stay away from the game, referring to their repeated mistakes or challenges in life. The chorus repeats the notion of feeling ashamed for a long time, while acknowledging that the presence of the person they are singing to is the reason they continue to push forward. The song also makes references to being trapped in a self-created hell and accepting blame for their actions. The line "here's the look but don't stare" suggests that the protagonist acknowledges their faults but does not want others to judge them solely based on their mistakes. Overall, "Ashamed" is a reflection on personal struggles, regret, and the hope that comes from having someone to lean on. It delves into the complexities of shame and the desire to break free from the negative patterns one has created for themselves.