The teen, it seems, wanted to ask the Florida governor an earnest question. “I can’t legally vote,” the 15-year-old said to Ron DeSantis at an Iowa coffee shop recently.

“It’s never stopped the other party from not letting you vote,” DeSantis interjected.

I think he was trying to say “from letting you vote,” meaning that Democrats supposedly allow 15-year-olds to vote illegally. (DeSantis’s campaign did not respond to a request for comment.) But he bungled his words, and either way, this is not a good joke. It’s especially not a good joke when you consider the second half of the teen’s sentence: “But I struggle with major depressive disorder.” Oof.

[Helen Lewis: The humiliation of Ron DeSantis]

This wasn’t an isolated moment of interpersonal clumsiness. On the campaign trail, DeSantis frequently behaves like he’s been dragged to a house party and is counting the seconds until he can look at his phone. He dryly remarked to an Icee-slurping kid, “That’s probably a lot of sugar,” and to a crowd of gathered fans that it was past his bedtime. When a reporter asked why he wasn’t taking questions, he snapped, “Are you blind?” He has a strange laugh that transforms abruptly into an okay-what’s-next industriousness. He passes up even obvious opportunities to show empathy, like when an 81-year-old veteran struggled to read the Pledge of Allegiance at his inauguration as Florida governor. Rather than take the man’s arm and offer help, my colleague Helen Lewis wrote, “DeSantis stood rigid and stern.”

I may not like DeSantis’s policies, but I deeply identify with his affect: Annoyed! Tactless! Maladroit! The New Yorker described him as “at his best on paper” and “a man so aloof that he sometimes finds it difficult to carry on a conversation.” He reportedly, and relatably, likes to keep his earbuds in so that people don’t talk to him. During debate prep years ago, an adviser told DeSantis to write a reminder on his legal pad: “LIKABLE.”

It’s somewhat of a given that DeSantis’s awkwardness undermines him, as it does for similarly stilted candidates. But the fact that voters care so much about a candidate’s smoothness is odd; awkwardness is not, per se, a bad thing. Most of us are a little awkward sometimes, or at least were a little awkward at one time. Some of the country’s most successful business leaders—Bill Gates, say, or Mark Zuckerberg—have a robotic quality, but that hasn’t stopped them. Social dexterity is something we expect of our presidential candidates, but of practically no one else.

It’s not just Democrats who find DeSantis socially awkward. “Ron DeSantis’s problem is that he finds it very difficult to work with people, or make people feel appreciated,” says Whit Ayres, the president of North Star Opinion Research, which polled for DeSantis in 2018.

Sarah Longwell, a pollster who runs focus groups of former Trump voters, told me that one group participant recently described DeSantis as “wooden.” Another, who actually liked DeSantis, called him “fine.” Longwell often asks people whom they would want if Trump isn’t the nominee. “In the last two groups, nobody has brought up DeSantis as the alternative,” Longwell told me.

DeSantis is the latest in a long line of candidates thwarted by awkwardness. It’s a problem some presidential hopefuls bring on themselves. When Jeb Bush, scion and supposed shoo-in, begged people to “please clap” at his carefully written applause line, he revealed a sheen of sweaty desperation. Onetime Republican presidential hopeful Mitt Romney’s attempts to connect with the common man resulted in him praising the “right heights” of trees and asking a crowd of Black voters, “Who let the dogs out?” At the 2000 Democratic National Convention, Vice President Al Gore tried to warm up his chilly image by giving his wife a big kiss—too big, it turned out. Hillary Clinton faced repulsive sexism and unfair treatment throughout her political life, but she also struggled to break out of white-paper speak. When she did—and here again I sympathize!—she could come off as haughty and superior, à la the “basket of deplorables.”

Other candidates, though, get struck by awkwardness through little fault of their own. They suffer the consequences nonetheless. At a loud rally in Iowa in 2004, Howard Dean hollered over the background noise into a unidirectional mic, and thus produced the first political meme to go viral (in a bad way). Later that year, the Democratic presidential nominee, John Kerry, fatefully went windsurfing, which is supposed to make you look cool, but instead made him look like a highfalutin flip-flopper when George W. Bush used the footage in an attack ad. Ted Cruz has somehow acquired a permanent pall of creepiness, helped along by a Twitter meme that he might be the Zodiac killer. (He’s not.) “His expression unsettles me,” one neurologist said when analyzing the senator’s tight little smile.

Awkward candidates have triumphed in the past: Richard Nixon, not exactly a people person, got elected twice. And it seems to be less of a burden for non-presidential offices: As Florida governor, DeSantis won reelection handily in 2022. Romney was governor of Massachusetts, and is now a senator from Utah. Hillary Clinton was a senator and the secretary of state, as was John Kerry.

But awkwardness proves fatal for many presidential candidates. Michael Dukakis, a perfectly competent Massachusetts governor, lost the election to George H. W. Bush after he was photographed riding in a tank while wearing a helmet. (In this case, too, the elder Bush looped the tank ride in an attack ad.) The governor’s advance team knew that the headgear would make him look “goofy,” but they failed to persuade him not to wear it. The aftershocks of that one rippled through politics for decades: Years later, President Barack Obama would decline to don a football helmet for a photo op. “You don’t put stuff on your head if you’re president,” he said. It just looks awkward.

[Mark Leibovich: Ron DeSantis’s joyless ride]

Like that other thing, you know awkwardness when you see it, and voters can see it over and over, anytime they come across a screen. Political news largely travels through TV and social media, two visual platforms that highlight every fake smile and weird comment. “The candidate who is most comfortable in the dominant medium of the time is most likely to be the candidate who is going to gain popular support,” says Kathleen Hall Jamieson, a political-communication expert at the University of Pennsylvania. Reporters like me also play a role, highlighting narratives that (sometimes) take off among voters. President Joe Biden’s many gaffes could be seen as awkward, and I could just as easily have written this article about him, after all.

It’s surprising, though, that voters care about awkwardness, a benign and universal human quality. Who hasn’t accidentally responded to a “Happy birthday!” with “You too”? Being a white-paper-oriented, small-talk-averse introvert can have its upsides. The presidency is a hard job, requiring intricate knowledge of the world’s largest economy and strongest military, plus a few dozen ever-evolving terror groups and simmering crises. It involves a fair amount of glad-handing, but also a lot of reading and thinking. Research has shown that introverts can sometimes be more effective leaders, because they’re more likely to listen to their subordinates. “They can capture information that some extroverts might overlook,” write the researchers Karl Moore and Willing Li. Awkwardness is associated with a sharp focus on details and an enthusiasm for interests, both helpful qualities in a leader. Meanwhile, confidence can sometimes steer you wrong: George W. Bush, with whom everyone wanted to have a beer, made some disastrous decisions on the basis of pluck.

So why do we care if the president is awkward? Partly, it’s because the presidency is also performative, and we want to be sure our pick can perform well. “The American presidency combines the role of head of government, a role that requires policy chops and managerial smarts, with the role of head of state, a role where you are expected to channel the hopes and dreams of everyday Americans and represent those people on the world stage,” Kristen Soltis Anderson, a pollster and co-founder of Echelon Insights, told me via email. We expect presidential candidates to handle the Middle East but also a pork on a stick. “While in other countries, being a bit dry or awkward might not be such a problem on the path to being Prime Minister, we in the U.S. expect our president to both understand what average people are going through while also expecting them to be anything but average themselves,” Soltis said.

Voters prefer candidates who have personality traits they value in themselves. We want someone who just is like us, but “more of a leader,” to quote one study. Hip, compassionate liberals gravitated toward Obama, a cool empath. Trump’s supporters often say the famous billionaire is somehow “just like them.” Most people are sometimes awkward, but awkwardness is not a state that’s valued. To be awkward is human, but we want our politicians to be superhuman.

The opposite of awkward is something like “charismatic,” which political psychologists tend to define as someone who speaks in stories and metaphors, and who can successfully transmit values that voters want to hear. John Antonakis, a professor of organizational behavior at the University of Lausanne, in Switzerland, has found that charismatic candidates do especially well in situations of “attributional ambiguity,” when it’s unclear whether their policy performance is strong or weak. (This may explain the remarkable rise of the charismatic, record-free Trump.) In the absence of better information, “voters will turn to see Who more resembles my prototype of ‘what is a good leader’?” Antonakis told me. He’s also found that smarter people are better able to produce charismatic rhetoric when prompted, so perhaps voters assume that charismatic candidates know their stuff.

Charisma is important not just because voters like smooth talkers, but because it makes candidates seem more authentic—which is what many voters, especially Republicans, look for. “That’s what happens with the woodenness, or the inability to have a comfortable smile, or a normal conversation with a human, is that you don’t seem like an authentic kind of person,” Longwell said. Voters tend to find Trump very authentic, but toward DeSantis, they use phrases like “unable to trust him,” she noted. The Dukakis tank moment was so hilarious precisely because it made the governor seem like “something he wasn’t,” as Josh King put it in Politico.

Awkwardness, then, might be a sign of a candidate’s unease in his role, a subtle clue that he’s only pretending to get it. “Awkwardness is the feeling we get when someone’s presentation of themselves … is shown to be incompatible with reality in a way that can’t be smoothed over with a little white lie,” writes Melissa Dahl in Cringeworthy, her book on awkwardness. Voters had trouble buying Dukakis as a macho tank gunner; they don’t believe that DeSantis would genuinely enjoy small talk. If a candidate looks out of place among presidential contenders, we think, maybe that’s because he is.

America loves an underdog, but perhaps not as much as it loves to watch a tumbling Icarus. No one’s wings have melted more dramatically and publicly over the past few months than Ron DeSantis’s. Eight months ago, the Florida governor was the man who would finally finish Donald Trump. Today he’s scraping to keep ahead of Vivek Ramaswamy, whom hardly anyone had heard of until recently.

Nearly every day, DeSantis seems to have some new problem. A New York Times poll published on Monday shows Trump with a commanding lead over DeSantis, and the specific breakdown of voter attitudes and profiles shows why it will be so hard for DeSantis to close that gap. DeSantis is in the midst of what is described as a campaign reboot but looks mostly like a mass firing, with the same old talking points and approaches—and, most important, the same old candidate. Trump has happily exploited DeSantis’s weaknesses, saying he has “no personality” and boasting in June, “Since Ron DeSanctimonious announced his candidacy, he has wasted over $15 million just so he can drop into nearly single digits.”

For anyone on the left side of American politics, this has provided a queasy schadenfreude. DeSantis’s exceptionally effective implementation of hard-right policies in Florida and his overt antagonism toward the media had made him seem like a figure of unusual promise and danger. Seeing Trump run circles around DeSantis with an ease not on display since the 2016 GOP primary has been entertaining to watch, but it’s a tainted pleasure, because the likely result is Trump as the Republican nominee—with a real chance of becoming president again.

[Helen Lewis: The humiliation of Ron DeSantis]

A few months ago, a lively debate took place in certain precincts over who would be worse for American democracy, President DeSantis or a reprise of President Trump. On the one hand, Trump has no respect for democratic institutions or rule of law and already attempted an autogolpe; on the other, his administration was characterized by frequent buffoonery and failure to execute. DeSantis, for his part, looked somewhat more like a normal conservative Republican, but his selling point was that unlike Trump, he actually knew how to get results, as his Florida résumé demonstrated—meaning he might be better at putting extreme policies into place. That debate faded a bit as DeSantis moved hard right, signing a very strict abortion law and escalating his feud with Disney, but mostly it has faded as DeSantis seems less and less likely to defeat Trump.

DeSantis’s collapse has happened in part because he may just not be a very good politician. The hard-right turn and falling polls are not unrelated; he’s pursuing ideas that most Republicans don’t support, much less most voters. The more voters see of him, the less they want to elect him. In a famous formulation, Americans want leaders with whom they can imagine drinking a beer. DeSantis comes across as the kind of guy who would lecture you about the empty calories in your glass, glower while he hurriedly gulped some non–AB InBev product, and then depart abruptly, leaving a bad tip. As Nate Silver recently pointed out, DeSantis’s electoral record isn’t great. His 2022 performance was impressive, but in his other four races, he’s run behind a generic Republican. Trump likes to say that he made DeSantis’s career with his endorsement in the 2018 Florida governor’s race, and he might have a point.

Which leads to the other big factor in DeSantis’s poor showing: Trump has been very good at beating him up. In 2018, 2020, and 2022, Trump led the Republican Party to defeat, so not since 2016 have we seen Trump demonstrating his full ability to shred an opponent. There’s something satisfying about watching an artist at work, even when that work is petty bullying of political rivals. Although he upset Hillary Clinton in the 2016 general election, he’s always been best at taking down fellow Republicans, so perhaps it’s no surprise that he’s so good at undermining DeSantis.

DeSantis (and other GOP candidates) is rightly afraid to attack Trump at the risk of alienating his base, but can’t afford not to attack him in order to draw a distinction. Either way, he can’t win. When DeSantis has echoed Trump, the former president has mocked him as a cheap knockoff. When DeSantis has (cautiously) criticized him, Trump has quoted DeSantis’s past agreement. When DeSantis has tried to outflank Trump to the right, Trump has mostly stood to the side and watched. (That’s a good reminder that although Trump governed as an aspiring authoritarian, the Republican field was to the right of him on many issues in 2016.) Trump has reveled in racking up endorsements from officeholders—and especially in snatching those of most Florida Republicans from right under DeSantis’s nose.

[Mark Leibovich: Just wait until you get to know Ron DeSantis]

None of the liberal glee at watching Trump skewer DeSantis reflects newfound affection for the former president. There’s no Republican candidate whom Democrats would actually like (you can bet that the progressive crush on Chris Christie would evaporate quickly if he were out talking about his policy ideas rather than attacking Trump). But many people in both parties believe that Trump would be the weakest possible Republican candidate in 2024—and that leaves many Democrats in the strange position of rooting for Trump in the primary.

Trump may not be as weak as his detractors imagine, or, at the very least, DeSantis may be no stronger. DeSantis’s wooden personality, very conservative platform, and pathetic performance thus far are enough to make one wonder whether he’d make Michael Dukakis look like a strong general-election candidate. Even if Trump is a weak candidate, the general election will likely be decided by a very few percentage points and perhaps just tens of thousands of votes in key states. Given the vagaries of the economy, President Joe Biden’s age and tendency toward gaffes, and the randomness of any election, Trump could very well win, inaugurating a disastrous second presidency. Liberals can’t in good faith pull for either man in the primary. In contemporary American politics, the enemy of my enemy is still my enemy.