Every icon begins as a person — vulnerable, impulsive, and brimming with dreams too large for their moment. Long before Sir Cliff Richard became one of Britain’s most enduring pop legends, before the fame, the polished interviews, and the knighted title, there was a young man named Harry Webb, aged twenty, standing beneath the window of a girl he adored. That girl was Carol Costa, and their relationship would remain one of the most intimate, yet quietly hidden, chapters of his early life.
In 1958, Carol first met Cliff when she escorted her younger sister to a concert at London’s Trocadero Empire. Jet Harris of The Shadows noticed the striking young blonde sipping Coca-Cola at the bar and introduced her to the newcomer — a teenage singer then still finding his voice. The meeting sparked a romance that was as passionate as it was pure. Cliff, the emerging star, found in Carol a calm anchor amid the first tremors of fame. He would visit her home, meet her family, and spend long evenings envisioning a future together — leafing through Country Life magazine and pointing out dream houses where they might one day live.
To Carol, these were not idle fantasies. “Everything we talked about made me believe we’d spend our lives together,” she would later recall. For her, Cliff was not yet the global performer, but a gentle, attentive young man who cared deeply and laughed easily. He visited her grandmother in the hospital in disguise, slipping in quietly with his dark glasses to avoid attention. In those moments, he was simply Harry — the boy with the guitar and a heart full of promise.
But fame changes everything. As Cliff’s career soared, propelled by hits like Move It and Living Doll, life began to pull him in another direction. In June 1959, Carol married Jet Harris — a union that quickly unraveled when she discovered his infidelity. Cliff, ever the caring soul, called her soon after, concerned not as a jealous ex-lover but as an old friend who still wished her peace.
Years later, when Cliff wrote briefly of the affair in his biography, his recollection was almost dismissive — labeling it an “infatuation.” Yet for Carol, it was more than that. It was her youth, her first great love, the spark that shaped both their emotional beginnings. She held the secret for over two decades, not out of shame but respect — for the man she once believed she would marry.
Even now, as Sir Cliff Richard continues to tour and record well into his eighties, that early story adds a layer of humanity to the myth. Behind the immaculate performer stands the memory of a young man throwing pebbles at a bedroom window, dreaming of forever with a girl in curlers.
It is in these forgotten details — the laughter, the long drives, the innocent belief in lasting love — that we find the real essence of Cliff Richard. His life was not merely a chronicle of chart-toppers and films but also of tender beginnings that shaped the artist he became. Carol Costa’s story reminds us that even legends begin with love, vulnerability, and the simple, timeless hope of being understood.
