In a routine, he serenaded the young woman and ended their song with “a little kiss”. In his autobiography Cliff Richard: The Dreamer, which came out last year, he described Ms Wicks as “a great girl”. He noted that they “had to keep a low profile” so his possessive fans wouldn’t find out about her. Cliff Richard's mother allegedly warned his ex-girlfriend not to 'get too fond' of the singer (Image: GETTY / WOW PRODUCTIONS) Cliff Richard dated Delia Wicks for less than a year before he broke up with her with a letter (Image: WOW PRODUCTIONS) Sir Cliff claimed to have sent Ms Wicks a postcard “from every town” during his tour of Scandinavia but soon their relationship fizzled out.