In Sinclair Lewis's book "Free Air," the author presents a humorous yet profound exploration of social norms and etiquette through two pressing dilemmas. One scenario poses the question of which is more socially awkward: attending a party in formal attire while everyone else is dressed casually, or showing up in casual clothes where formal wear is the expectation. This highlights the anxiety people feel regarding conformity and social acceptance, emphasizing how important appearances are in social interactions.

Additionally, Lewis examines the complexities of tipping culture with a similar lens. He raises the dilemma of whether it is worse to neglect tipping when it is anticipated or to give a tip that could be deemed insulting. This adds a layer of tension surrounding social obligations and the potential repercussions of failings in etiquette. Through these questions, Lewis invites readers to reflect on the often-unacknowledged pressures of societal expectations.