Hey @peeps! Check out this hecka-cool #Jeb! #Website!

A still from one of Jeb Bush’s #NoFilter videos. (Photo: Via YouTube)

Jeb Bush’s YouTube page, like that of any other presidential hopeful, is filled with clips that are meant to make him look good. There’s the moment he asked Trump to apologize to his wife during the Sept.16th Republican debate. And there’s an ad detailing his strong economic record in Florida. But then, uh, there’s also that playlist of videos titled #JebNoFilter.

As you might guess from its tragically hip name, the collection of short clips is meant to show off the former Florida governor’s more spontaneous, more human side. Sort of like that time Beyoncé adopted alter ego “Sasha Fierce” to promote her album — only exceedingly less glamorous.

In “Hoodie” — a 30-second clip with over 17,000 views — Bush struggles to put on a souvenir from a startup he visited, pulling its hood over his eyes and grinning widely before saying, “Eat your heart out, Zuckerberg.” In another, he reveals his worst Father’s Day gift — a weight-loss book from his sons — saying it made him feel “offended and embarrassed,” then staring straight into the camera and laughing uncomfortably. In an overproduced video titled “ Silicon Valley Favorites,” Bush answers a series of either/or questions about his favorite technology and reveals, boringly, that he owns several Apple products and prefers #FollowFriday over #ThrowbackThursday. Needless to say, these segments have been excellent fodder for the nation’s Vine-makers.

Jeb’s team may have hoped to project a cool, tech-savvy persona, but misdirected content like this has the opposite effect. Neither crazy enough to be entertaining, or policy-heavy enough to be wonky, they strike a pandering, out-of-touch tone. The 62-year-old grandfather’s message to any discerning young onlooker might as well be, as one YouTube commenter put it, “How do you do, fellow kids?”

Bush, to be fair, is not the only presidential candidate to attempt and fail to seem “fun.” (Just ask the Onion.) But after his tepid performance during the third Republican primary debate and the news that he downsized his campaign spending for a second time, the once-promising GOP contender’s digital presence is more important to his campaign than ever. Despite his glossy video output, his forthcoming e-book of emails, and a steady flow of Twitter, Facebook and Instagram posts, Bush has failed to garner the kind of online grassroots support that Donald Trump and Ben Carson enjoy. His failure is due not to lack of resources, effort or quality of content, but a ho-hum personal brand and a few damaging viral missteps that have revealed his try-hard inauthenticity.

The Internet, and the highly sought-after millennials who spend a lot of time on it, crave authenticity. As Wired’s Issie Lapowsky wrote earlier this month, many campaigns mistakenly operate “as if the way to engage a digital-savvy generation of young voters is to talk to them the way they talk to each other.” But, she said, “these young voters see right through it.” Thus, the snickering that greeted Jeb’s run-in with a hoodie.

But being a part of the Bush empire leaves the candidate in tricky territory. If young people crave authenticity, then he should just be himself. But that would mean being completely honest about his elite Eastern establishment pedigree, thus evoking his inherent privilege, not to mention the unpopular military decisions of his brother and dad.

To sidestep those challenges, Bush’s team has settled on an image that straddles the line between policy nerd and humble family man, touting his record as Florida governor in ads and testimonials and emphasizing his tech-savvy accessibility by teasing a forthcoming e-book of all his emails back and forth to Floridians (even if no millennial will ever read it). But because they seem petrified of a misstep in the current political environment, their strategy often comes off as incredibly bland or strangely out-of-character.

These subtle but telling digital blunders have seriously undercut his cooked-up personal brand. They could be seen in microcosm during the third Republican debate. The candidate’s digital team was present on the majority of mainstream digital avenues: his website featured a well-designed “debate night” page, including small Vox-like card stacks that conveyed basic “facts” about Bush’s views on immigration, education, Planned Parenthood and so on. Subscribers to his email list received a barrage of emails Wednesday night, imploring voters to contribute to his “debate response fund.” His Twitter and Facebook feeds were updated frequently, at a Social Media Manager-Approved™ pace. Bush even posted a decent Instagram, displaying the pair of Jeb-branded “debating boots” he was wearing to the Boulder, Colo., event.

But the actual content of these messages was cautious, verging on boilerplate. “Jeb has a clear plan & conservative vision to reform Washington & jumpstart the anemic Obama economy,” read one tweet. “If you want somebody that has a proven record, elect me so I can fight for the American people and change the culture in Washington, D.C.,” a Facebook post declared. These are so generic that they could’ve appeared online at literally any time during the entire election.

Meanwhile, several emails encouraged subscribers to share the campaign’s prefab statements about Jeb to their own pages, excessively hash-tagged opinions like “Gov. @JebBush cut #taxes by $19 billion + created 1.3 million jobs in #FL, as #POTUS he’ll fix our broken #economy. #AllInForJeb.” This is the type of thing any young person with even the slightest sense of a personal brand would be loathe to do. Canned posts, in their eyes, are an embarrassing thing their parents do on Facebook, the equivalent of an annoying Farmville invite or forwarded chain email.

But perhaps more damaging to his presence online was the complete dissonance between what was actually happening in the debate and what was going on in the many Bush feeds. Yes, his campaign shared a few quotes from the stage. But when the candidate offered “a warm kiss” to any Democrat who cut spending by $10 — probably the first real moment of personality — his staff made no explicit mention of it, instead sharing a quick clip of it and moving on. Nevertheless, BuzzFeed reported the Internet’s reaction with a post headlined “Jeb Bush Offered A Warm Kiss And The Internet Collectively Threw Up A Little Bit,” declaring that a “warm kiss is the new moist.” Politico included it in its “ 9 awkward GOP debate moments” roundup. It was immediately unflatteringly Vined and GIFed.

It was an awkward moment, but it was real. Any young person can relate to saying something weird or embarrassing by accident. If his campaign had owned that moment — made a self-deprecating crack or acknowledged the Internet’s reaction — maybe the response wouldn’t have been as harsh. He would have at least seemed more self-aware and in on the joke. Instead, his staff’s judgment of the gaffe was apparent, and it came off as something they wanted to forget altogether.

After last night’s debate, Bush sat down with CNN’s Dana Bash to hash it out. She mentioned Twitter. “I don’t follow Twitter,” he countered. “I don’t worry about it. I’m going to control the part that I can control.” But what Bush and, apparently, his digital team don’t get, is they can control parts of it. Acknowledging real-life moments with humility, and less of an iron shell of professionalism can make a person seem relatable, and even earn you defenders. That’s the way you connect with your base. Not with video of you trying on a hoodie.