There is little time spent in the film before we learn that Gil is a lover of aesthetic detail, and that he is dissatisfied with the superficial turn that his career as a writer has taken in spite of himself. The love of his life happens to be an educated material girl, whose depths of interest, limited to prestige and the all-American rightist point of view, do not include the spice of life that Gil seeks in the streets of Paris. As structural opposites, they represent what exists as modern materialist American culture, and a longing for the artistic soul that appears to be lost into generations past.
As a film writer, Gil Pender has experienced the demands of Hollywood that can easily turn a beloved art form into the mundane reproduction of generic manuscripts that lack acknowledgment of individual style. His retreat from his career's successes, then, is his voluntary conversion to novel-writing, a venture through which he must learn to detach his professional logical practices in order to have his work flourish.
And so he looks to 1920's Paris. The adventures into which a midnight carriages take him expose Gil to a pre-technological-addiction era where the arts and romance are more relevant than shopping sprees and prenuptial agreements. The essence of beauty is herein redefined for Gil, as he immerses himself into the lives and influence of such artists as Hemingway, Stein, Picasso, Fitzgerald, and Cousteau, and finds love again in the form of an aspiring costume designer who admires his work.
The return of Gil's literary confidence unavoidably comes at the price of his engagement to Inez, who has fallen for an old college friend as he simultaneously falls for the 1920's beauty Adriana. Although still blinded by his artistic rejuvenation and the intrigue of a new muse, Gil begins to process the inevitable truths about his lifestyle that reveal themselves through the wisdom and advice of his heroes.
True to the stylistics of Woody Allen, our protagonist finds himself after some character-pruning afforded to him by his nighttime adventures in a world not yet consumed by globalization, mass film production, and apparently, antibiotics. Gil's epiphanic moment of clarity in his visit to the nineteenth century with Adriana opens his eyes to the possibility of enjoying his life outside of nostalgic illusions, and thus allows him to break free from professional and social expectations that hindered both his creativity and his happiness.