The Irony of Romance
Jimmy would engage prostitutes and explore their stories. He would then romance them depending on how they could relate to Gloria. As this story unfolds, at one point we see Jimmy in possession of Gloria. Ironically, this story also strongly implies that Gloria never existed.
The Irony of Existence
The more Jimmy searches for Gloria the more she makes herself scarce. Gloria is always almost within the reach for Jimmy but just beyond what he can conceptualize into reality. Gloria’s image seems to be distilled from Jimmy’s memory and fantasy, and she might or might not exist in real life.
The Irony of Personality
For someone who had been in service in Vietnam like Jimmy, we expect someone of an astounding character in the society. Jimmy rather engage prostitutes while trying to fulfill his fantasies about Gloria. This goes against the morals that we presume were instilled in him having been an important figure in society.
The Irony of Confusion
Jimmy idealizes Gloria and presumably presents her as perfect. Ironically, he goes looking for her among the whores. The story of Gloria is not clear and we are not sure if she exists or she is an imagination.
The Irony of Priority
Jimmy spends his last dollars of retirement benefits in the bars engaging prostitutes while searching for Gloria. His main motivation to be in bars is not to enjoy. He is motivated to find Gloria through the prostitutes.