'The Sussexes embody the great tragedy of the Millennial.' Chris Jackson/Getty Images

Somewhere in Montecito on Sunday, a balding Englishman will celebrate his birthday over a bold Tignanello, clinking glasses with his glamorous Californian wife. Like Footloose, Agadoo and the original Apple Mac, Prince Harry is turning 40 — leaving behind a torrid decade of public spats, todger confessions and expensive therapists.
Nothing quite boils the blood of middle-aged men more than the departure of the Duke of Sussex for a better life out West, an upside-down Steinbeck protagonist. Most will claim to be enraged by the duke’s abandonment of duty or some such sniffy notion, but we all know that his great crime — greater even than that suggestion that his wife once made the sainted Princess of Wales cry over bridesmaid dresses — is self-involvement. His 2021 interview with Oprah alongside his wife Meghan confirmed our most sickening fears: that the toxic creed of “speaking your truth” had become irreversibly lodged in good old Harry Windsor’s brain.
Despite having two of the most unpopular qualities in British culture — he is, after all, a ginger posho — Harry was always respected among the bulk of the public (who, we must remember, regard the royal family with nothing more and nothing less than detached, bemused affection). He was the light relief to William’s sombre nobility, the cheeky spare who winked at Noughties lad culture and seemed to enjoy his privilege rather than wince at it, frolicking around in states of controversial dress (or undress) and injecting a sense of normality — fun, even — into a unit which had been so wracked by tragedy and, worse, off-putting stuffiness.
But his capture by millennial therapy culture signalled the death of this happy-go-lucky persona. For those who once grinned that Harry was a “rum lad”, this was a personal affront precisely because of the loss of that pleasing irony, the sauciness and levity which turns even bluebloods into good drinking partners. When the winks stopped, we sobered up and realised we had been sat opposite a quiffed clown, made up to look like a cheeky friend. The slipping of that mask must have hurt — particularly among those middle-aged men, for whom any association with the touchy-feely bollocks of California is not just embarrassing, but offensive.
Prince Harry is, without a doubt, the most millennial millennial to ever have breathed. In his trajectory from cheeky chappy to earnest, self-regarding counselling patient lies the story of his generation’s downfall into cringe. Though he sees his transformation as a journey to his authentic self, it is crystal clear to everyone not living under the glass dome of American therapy-speak that he has simply journeyed from one posture to another, each freighted with unbearable artifice. For the first, 1,000 years of monarchy and the straitjacket of the British class system determined his route from genteel thicko (he left Eton with a B in art, a D in geography and a dash of notoriety for smoking weed) to Army to nice girlfriend called Cressida. Had he been a commoner, he would have ended up as a mid-level consultant in Putney, probably in the shadow of his barrister brother William. Raffles has lost a lot of custom since his enlightenment.
But this second, new persona — one which he hard-launched with the Oprah interview — is no less fated. With the awakening of West Coast elites comes a compulsory set of fixations, which I like to imagine their shrinks laugh about together at dinner parties. First and foremost, the wrongs of your parents, childhood trauma. Of course, Harry has more of this than most, and that is fair enough. But the endless remonstrations with your family, friends and “support network” — and a compulsion to cut them out for historical wrongs — is so distinctively millennial, and something which Abigail Shrier has rightly identified as having engendered complexes and neuroses in people who, for the most part, would have otherwise chugged along without a problem. Harry represents the great millennial task of seeing yourself as a kind of project, and the fallacy that it is not what you do, but how you feel about what you do, which matters.
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