The narrator of the song is struggling to get over someone, staying up late thinking of ways to remove them from their mind. Despite trying to avoid memories and reminders of the person, they find it difficult to escape the thoughts of them, even in their dreams.

Meaning of "Stayin' up Late (Thinkin' About it)" by Dwight Yoakam

The lyrics of "Stayin' up Late (Thinkin' About it)" by Dwight Yoakam depict the deep emotional struggle of trying to move on from someone who has left a significant impact on the narrator's life. The constant battle between the desire to forget and the inability to fully erase memories is a universal theme many can relate to. The late-night rumination and haunted dreams showcase the internal turmoil and the desperate attempts to find closure and peace of mind. The reference to avoiding pictures, memories, and everyday triggers further emphasizes the difficulty of letting go and the yearning to break free from the hold of a past relationship. The nostalgia of riding in cars together symbolizes the shared experiences and moments that are hard to detach from. Overall, the song captures the raw, complex emotions of heartache and the enduring struggle to move forward while being stuck in the past.