As the Eskimos were said to have seven words for snow, today’s Americans have a near-infinite vocabulary for gradations of awkwardness—there are some six hundred entries in Urban Dictionary. We have Awktoberfest (awkwardness that seems to last a whole month), Awk and Pshaw (a reference to “shock and awe”), and, perhaps inevitably, Awkschwitz (awkwardness worthy of comparison to the Holocaust). We have a hand signal for awkwardness, and we frame many thoughts and observations with “that awkward moment when…” When did awkwardness become so important to us? And why?

In “Awkwardness: An Essay” (2010), the critic Adam Kotsko dates our age of awkwardness—embodied by “the apparently ontological awkwardness of George W. Bush” and manifested in television shows like “The Office,” “Arrested Development,” and “Curb Your Enthusiasm”—to the early aughts, with a postwar prehistory. (In short, Kotsko writes, the fifties purveyed capitalism into an ideology of “traditional Christian values”; in the sixties, these values were destabilized by the counterculture movement; the ideological vacuum of the seventies led to the paranoia and nihilism, reflected in the metaphysical being of Woody Allen; in the eighties, pure capitalism became its own value system, sustained by opposition to the Soviet Union; and in the nineties nihilism returned, minus the Cold War paranoia, inaugurating the age of irony.)

What caused the shift from irony to awkwardness? Interestingly, Kotsko refuses to blame September 11th, connecting the end of irony less with “a culture-wide turn towards earnestness and patriotism” than with irony having “simply exhausted itself.” My feeling, however, is that we can peg the end of irony to September 11th precisely because of the failure of “earnestness and patriotism” that Kotsko describes. We finally had an “evil opponent” again. Terrorists, like Communists, hated “our way of life.” If we neglected our Christmas shopping, Bush said, the terrorists would win. But, this time, the rhetoric didn’t stick. The U.S.S.R. had been a nuclear superpower, with geopolitical aims comparable, if opposed, to those of the U.S. Al Qaeda was nationless, nihilistic, and armed with box cutters. You couldn’t lump it together with North Korea and call it the Axis of Evil—that didn’t make sense.

If, for a moment, it seemed that September 11th could be identified with Iraq, the illusion was short-lived. As evidence of Iraq’s weapons of mass destruction, or of its involvement in September 11th, failed to materialize, it became increasingly clear that the 2003 Iraq invasion was about profit and not about evil, and that’s when the awkwardness really set in (Awk and Pshaw). I remember how awkward it felt to buy a new computer or to read Pushkin—though I did those things anyway, and kept collecting my grad-school stipend. Sometimes, I would see people driving in cars—cars—with “Not in My Name” bumper stickers, and I would feel a deep sense of unreality. Awkwardness is the consciousness of a false position.

Here is the top-rated definition of awkward in Urban Dictionary: “Passing a homeless person on your way to a Coin Star machine.” In other words, denying that you have any spare change while carrying a whole jar of change, a transparent column of money, right in front of the person. In fairness, although there is a sense in which you can spare the change, there is also a sense in which you can’t. Who are you, after all—the one per cent? The one per cent doesn’t use the Coin Star machine.

“Awkward” implies both solidarity and implication. Nobody is exempt. Awkwardness comes from the realization that, when you look around the world, it’s difficult to identify anyone who isn’t either the victim or the beneficiary of injustice. Awkward moments remind us that we are never isolated individuals, and that we are seldom correct when we say, “Not in my name.” Awkward moments are, by definition, relatable. Hence the tagline for “Curb Your Enthusiasm”: “Deep inside you know you’re him.” This is a key distinction between Larry David’s comedy of awkwardness and its closest predecessor, Woody Allen’s comedy of anxiety. Anxiety is pathological, neurotic (a word you don’t see so much anymore); awkwardness is existential, universal.

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I decided to write about awkwardness when I heard Adam Gopnik tell a story about taking his eighteen-year-old son, Luke, to the steam bath in a gym on Fourteenth Street. Gopnik hopes to recreate his childhood experience of accompanying his grandfather to the Russian baths in Philadelphia, in the nineteen-sixties. This hope is dashed when Gopnik enters the steam room to find two men having sex. Although he dislikes the word “inappropriate,” associating it with his father’s generation of “whining Jews” (in contrast with his grandfather’s generation of “groaning Jews”), Gopnik feels that he has no choice but to send his son across the street to buy a donut so that can he complain to the management about the men’s “inappropriate behavior.” But, when he rejoins his son, he finds that Luke hasn’t been fooled; he saw the men in the bath, too, and has his own, completely different response: “That was awkward,” he says.

Shortly after hearing Gopnik’s story, I came across the following line in the “The Aspern Papers”: “I had been devilish awkward, as the young men say, to be found by Miss Bordereau in the dead of night examining the attachment of her bureau.” The publication date of the novella, 1888, is a valuable reminder that there were awkward moments long before there were Awkward Moments; that, for hundreds, even thousands, of years, fathers have said, “Inappropriate!” and sons have said, “Awkward!”

In a sense, all awkwardness is familial awkwardness. The nuclear family is a petri dish for awkward moments: traditionally, the one place where sex is condoned and the place where sexual urges are most vehemently patrolled. The family is a little island of people who aren’t supposed to have sexual feelings for each other (except for the parents who, in these circumstances, have their work cut out for themselves with the task of sustaining sexual feelings for one another). Any shared confrontation of sexuality by children and parents is painful, perhaps traumatic, and definitely awkward. The mysterious Biblical Curse of Ham, precipitated when Ham sees his father naked, may well have been family awkwardness. Is there a clue here to the “ontological awkwardness” of George W.? We knew his dad.

Whatever one thinks of the relationship between capitalism and the patriarchal family, both depend on a certain degree of hypocrisy in order to function smoothly. This is a recurring theme in the television drama “Mad Men”: it’s impossible not to liken the hypocrisy of Don Draper’s ad work—writing cigarette advertisements, say—with the sexual hypocrisies of family life. In a particularly awkward moment, Don’s daughter, Sally, is caught masturbating during a grade-school sleepover. Her mother, Betty, a housewife who has sought relief for her own sexual frustration from her washing machine, threatens to cut off her daughter’s fingers: “You don’t do [these things] in private, and you especially don’t do them in public!” Though “Mad Men” is set in the sixties, its obsessive hyperrealism and its frank depictions of sexual and political hypocrisies make the show a quintessential product of our age of awkwardness.

Sexual, intergenerational, and socioeconomic awkwardness all come into play in Gopnik’s story, particularly in the dichotomy of “groaning Jews” and “whining Jews.” “Whining Jews,” like Gopnik’s father, are eternally conflicted: “Every question about civil rights and women’s rights” is the subject of “Woody Allen”-style agonizing. “Groaning Jews,” like Gopnik’s grandfather, have no such agonies, and they are content to groan—perhaps monosyllabically—in the shvitz, emerging with renewed energy for their duties at work and at home. Gopnik pegs his interest in steam baths to a dream of transforming himself “from a whining Jew back into a groaning Jew.” But, of course, there is no going back to the serenity of the early sixties, and, of course, this is a good thing.

Gopnik sees awkwardness as “a great blessing”: a new form of equanimity. Instead of obsessing over “morals” or “behavior,” the new generation is “concerned only about grace.” Gopnik implies a turn away from outraged ethical judgment and toward tranquil aesthetic appreciation. But it’s important to note that grace in this context is also moral: you can’t be graceful when you’re in a false position. Somewhere in Luke’s “awkward” is a recognition of the plague and persecution suffered by homosexuals—an acknowledgment that, though the situation is improving and “family values” are broadening, there is still a long way to go and much awkwardness ahead.

A similar moral message may be found in Taylor Swift’s controversial new video, “Shake It Off,” in which Swift emphasizes her awkwardness compared to the black dancers in the video, as if to say, “I know my ancestors once enslaved your ancestors, and therefore I am physically and metaphysically less graceful than you.” That’s not a comfortable sentiment, and it brings us back to the notion of family awkwardness. Awkward moments have a way of pitting us against our own history, against the values of our fathers and grandfathers (cf. racist grandparent meme). But awkwardness is a small price to pay, considering that our present is more just than our past, and our future may be more just still.