Meaning of "Following Rita" by Train

"Following Rita" captures the essence of leaving someone or something behind and the emotional journey that comes with it. The imagery of driving away physically while feeling closer emotionally illustrates the complex nature of distance in relationships. The encounters with strangers like the toll booth operator and Elvis James McCabe symbolize the connections we make in fleeting moments that can leave a lasting impact. The mention of regret and missed opportunities with the two girls and their respective paths signifies the choices we make and the paths we take, often leading us to unexpected destinations. Overall, the song explores themes of separation, longing, self-discovery, and the bittersweet nature of change.