Keep on Trying

Song Meaning

Garland Jeffreys's "Keep on Trying" is a deceptively simple anthem of urban romanticism, cut through with a distinctly world-weary edge. On the surface, it's a straightforward plea for perseverance in the face of love's challenges, a sentiment as universal as the New York City streetlight under which the narrator stands. But the song meaning goes deeper, hinting at the psychological toll of relentless pursuit in a landscape where authenticity feels increasingly elusive. The repeated mantra of "Keep on tryin' baby" becomes less an encouragement and more a desperate self-affirmation against the backdrop of city alienation. Jeffreys, the "New York City kid," isn't just looking for love; he's looking for joy, a connection that transcends the transactional nature of modern relationships. He acknowledges the grind – "Gotta work it if you wanna' do it right" – but there's an underlying tension. The lyrics subtly introduce the idea of effort versus authenticity. He's a "hometown boy makes good," implying a level of success achieved through striving, yet he explicitly rejects the notion of hustling for love. This reveals a core conflict: the desire for genuine connection versus the pressure to perform and compete in the dating arena. The repetition of the chorus, while seemingly optimistic, underscores the repetitive, often futile nature of the search for love. It’s a cyclical process of hope and disappointment, mirrored in the simple, almost hypnotic melody. The narrator is "dead tired on my feet," a detail that paints a picture of exhaustion and vulnerability. The "pretty girl I'd love to meet" is less a specific person and more a symbol of the idealized connection he craves, a connection he hopes to find without sacrificing his integrity in the process. Ultimately, "Keep on Trying" is a nuanced exploration of the tension between hope and disillusionment in the search for love, a theme that resonates deeply within the modern urban experience.