Jay Gatsby and J. Alfred Prufrock are two modern literary protagonists who’d probably never be caught dead in the same room together. Although both turn-of-the-century men are in love with utterly unattainable women, their attitudes toward life, the universe, and everything couldn’t be more opposite. Gatsby amasses a fortune, buys a mansion, throws lavish parties, and completely reinvents himself, taking the flamboyant peacock approach to wooing his ladyfriend. Prufrock, on the other hand, reluctantly initiates a meeting, hesitates, broods, retreats, and ultimately resigns himself to a life of isolation, taking more of a unabomber approach to courtship. Yes, ladies – sometimes these are your choices.

Although Jay and J. Alfred seem to live worlds apart, chronologically speaking, they are only separated by about a decade. In fact, both characters are pioneers of a cultural period that was shortsightedly dubbed “modernism” on the off chance that nothing would ever change again. With booming cities, huge crowds, division of labor, and division of wealth suddenly becoming commonplace, people experienced an unprecedented sense of isolation, disjointedness, and anonymity in the new cultural landscape. On some level, Gatsby’s and Prufrock’s troubled romances represent a larger struggle to find their place in early twentieth-century city life, which is strongly reflected in the way they’re each narrated.