Night was falling, and the waves were only getting bigger. Hurtling into the sea, in nothing but trunks, following a summer gay wedding on the beach: the nation’s number one scion.

Revelers screamed like geese. Half were drenched. Mobile phones were lost to the sea, including that of one of the grooms (a prominent anchorman at the time).

And, there, in Baywatch mode, as another rogue wave moved in, in Newfoundland: the closest thing to the late JFK Jr. that Canada has ever produced. His Romeo mane flattened and his torso glistening, Justin Trudeau had leapt into the treacherous waters to, well, carpe diem.

He’s been paddling fast ever since.

Five years have passed since the day I took in that scene, and now he’s in an even more furious swim: one for the office of Prime Minister, the highest office in the land.

In a national election well underway in Canada (yes, there’s an election happening north of the border, too!), his is a candidacy buoyed by not only his amazing sea-legs and his H&M-model looks, but a surname garlanded with destiny.

As famous inside his borders as that other Canadian Justin—Bieber—Trudeau, the current leader of Canada’s Liberal Party, is the son of a former prime minister. And not just that, but probably the most storied one in modern Canadian history.

Dad, Pierre—about whom a whole industry of remembrance subsists—was the man with the perennial rose in his lapel, one who ran the country for a combined 16 years, all the while altering “his country’s traditionally staid and fusty image with atypical flamboyance,” as The New York Times once put it.

Think of it as a nostalgia best channeled by Barbra Streisand, of all people, when she was last in Montreal, touring. An ex-flame of the elder Trudeau (a lothario of some skill in his time), she was tickled pink to see his son in the audience.

Giving him a call-out from the stage, I recall, she stopped just short of squeezing Justin’s cheeks. “So full of progressive ideas for the people,” Funny Girl gushed, predicting that, yup, he will be prime minister one day.

It’s a prediction, alas, that might not be winning Babs any money in a pool—at least, not this time ’round. Trailing in the polls, for an election set for October 19, Trudeau 2.0. remains in a tight squeeze between the sitting Conservatives, to the right, and the NDP party, to the left.

From the former—courtesy of incumbent PM, Stephen Harper—Trudeau continues to be badgered in ads that feed into a cliché of him as a dilettante, ones damning him with faint praise about his hair.

From the latter, via the party run by Thomas Mulcair’s band of progressives, he is being painted, likewise, as “naive.” However you slice it, even performing adequately enough in the first leaders’ debate didn’t help move the needle in his numbers.

“Everybody will want to sit beside him at the G7.” That’s what Chrystia Freeland tells me. A journalist and TV analyst of much renown, she was lured back to her native Canada to run for Parliament as a Liberal, and she was speaking, some time back, about Trudeau’s charm-offensives on the global stage.

The thing about all this, of course, is he needs to get through the hula-hoop of a national election first before he can razzle-dazzle internationally.

The source of his appeal is also his Achilles’s heel. For every Canadian who’s wooed by Trudeau’s youth, and his relative charisma, there are those who remain unpersuaded, or find it unctuous.

It’s a healthy vigor routine that passed well into caricature, a little while back, when Trudeau proved victorious, in a televised boxing match, for charity, against a Conservative colleague (an ex-soldier with a Black Belt!).

Trudeau took the rumble in the second round. This month, in a photo-op meant to echo that win, and to double-down on the metaphor, he threw on social media a photo of himself, the morning of the leaders’ debate, at a boxing ring.

Beyond the slew of policies he’s known for—fiscal overtures aimed at the middle-class, a proposal to legalize marijuana, an emphasis on more affordable child-care—it’s clear that Trudeau’s spryness is itself crucial to the campaign, an image only aided by the portrait of his young family: wife Sophie Gregoire-Trudeau, and their three children, Xavier, 7, Ella Grace, 6, and Hadrien, 1.

PR-wise, the missus—a former TV host in Quebec, as well as a recently certified yoga instructor—appears to be an asset. Sometime after a photo of the couple dancing, Pulp Fiction-style, backstage at an event went viral a while ago—and promptly turned into a zeitgeist-friendly GIF—a friend of the couple told me that the photo wasn’t as spontaneous as it appeared, and that savvy Sophie had plotted it. Ding!

But how hip is too hip? And how young is too young? It’s the psycho-subtext of the electoral race going on, once you get behind the conjecture and the punditry. It is the text, too, considering the main refrain that the Conservatives have going against Trudeau—over and over again—is, quote-unquote, “He’s Just Not Ready.”

Yet what’s even stranger about this all is the fact that Trudeau isn’t all that young, in the broader horizon of manhood. He’s 43 years old, for goodness sake. And his foe, Mr. Harper, a Liberal insider points out, was himself 45 when he won the prime ministership a decade ago.

It’s almost like Trudeau Jr. is a weird manifestation of the wonky relationship that the culture has with aging these days, in general—a culture where auteurs like Wes Anderson make films with child-like adults, and adult-like children, and where an unstoppable Tom Cruise continues to hang from planes in Mission Impossible movies, even well after his half-century birthday.

Yes, the Canadian scion sometimes plays into this himself with his propensity for gaffes. But there’s something more: because the Canadian scion is a looker (especially by politician standards) and because, moreover, many Canadians remember when he was born (he made his first steps at the official residence of the prime minister, 24 Sussex Drive), it’s like he’s not allowed to be a grown-up.

And his enemies haven’t exactly made it easier for him. Just look up the number of times “Peter Pan” and “Justin Trudeau” come up if you toss those two searches into Google.

Likewise, a headline in the usually buttoned-up Globe & Mail once read, “He’s sweet, but is Trudeau a PM?” The columnist at that national newspaper went on to write, “Mr. Trudeau is warm and nice and fuzzy. He doesn’t have an intellectual bone in his body.”

In an electoral bid already ensnared in the optics of nepotism (like both Hillary Clinton and Jeb Bush in the U.S.), can Justin make it out of Neverland? He has less than two months to make it happen.