Over more than six decades, Cliff Richard has been the golden voice of British music – and a man whose romantic life has sparked curiosity. Some relationships became media sensations, while others were kept secret for years. Here are 5 romances fans talk about the most, each tied to a special chapter of his life.


1. Delia Wicks – Young Love

In the early 1960s, Cliff fell for dancer Delia Wicks. As his career soared, he chose to part ways to focus on music. Years later, a heartfelt breakup letter revealed his deep regret.
Photo suggestion: Black-and-white shot of young Cliff smiling gently.

Cliff and Delia Wicks 1961

2. Olivia Newton-John – Friendship with a Spark

Through many collaborations, Cliff and Olivia formed a close bond. Though they never confirmed a romance, fans believe there was something more between them.
Photo suggestion: Cliff and Olivia together backstage.

Cliff Richard and Olivia Newton-John

3. Sue Barker – A Rare Public Romance

Tennis star Sue Barker was one of the few women Cliff openly dated. Their relationship lasted a few years before ending due to busy schedules.
Photo suggestion: Cliff with Sue Barker at an ’80s event.

Sue Barker finally lays bare the game, set and match of her romance with Cliff  Richard in new book | Daily Mail Online

4. Jackie Irving – Hollywood Glamour

Cliff was captivated by Jackie Irving, a well-known actress and dancer. Though brief, the romance left a mark on his most tender love songs.
Photo suggestion: Cliff in a formal suit at an international event.

Heyday Cliff with Ann Holloway and Cilla Black

5. Green Park Mystery Lady – The Untold Story

Rumors swirl about Cliff’s secret relationship with a non-showbiz woman, often seen strolling through Green Park, London. Her identity remains unconfirmed.
Photo suggestion: Cliff walking outdoors or artistic park setting.

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Conclusion

Though never married, Cliff Richard’s love life is filled with passion, heartbreak, and mystery – each adding depth to his timeless romantic ballads.

💬 Which of Cliff’s romances intrigues you most ?