Although he may sing about all things to do with love and heartbreak, Sir Cliff Richard's romantic life remains a bit of a mystery.
The 83-year-old has never married, having previously explained that his dedication to his music career simply took up too much time, and wouldn't, in his view, have been compatible with a happy marriage. Speaking with BBC News back in 2003, the music legend explained: "I've been in love... but marriage is a big commitment, and being an artist consumes a great deal of time."
There have however been a few 'false alarms' along the way for Sir Cliff, from the dancer whose heart he 'ruthlessly' broke, to the famous girlfriend who became sick of him 'harping on' about their relationship decades later...
Sports star girlfriend
Sir Cliff's best-known relationship was with tennis champ and TV presenter Sue Barker, whom he dated for a brief period back in the 1980s. The pair first locked eyes at a tennis tournament in 1981, and quickly bonded over their shared love of the sport, as well as their Christian faith. Although they had plenty in common, Sue had doubts about the 16-year age difference between them - Sir Cliff was 41 at the time while she was just 25. The sports star also wasn't keen on the intense scrutiny surrounding their courtship, which is understood to have lasted less than a year.
Things eventually cooled between the lovebirds and, according to Sue, Cliff ended up getting one of his pals to break things off with her for him. They briefly reconciled after Cliff contacted her out of the blue to admit that he missed her, but Sue quickly realised they were better off as friends.
Made in Chelsea star Ruby Adler dating drug dealer son of ex VIP dominatrixSir Cliff has spoken out on multiple occasions about his romance with Sue, now 67, once confessing that he had at one point wanted to propose but felt he 'didn't love her enough'. During a 2008 interview with the Mail Online, Sir Cliff claimed: "I seriously contemplated asking her to marry me, but in the end, I realised that I didn't love her quite enough to commit the rest of my life to her. There were no broken hearts."
Although the pair remain friends to this day, Sue, who is now married to landscape gardener Lance Tankard, has previously expressed frustrations about Sir Cliff continually 'harping on' about a relationship that she regarded as more of a friendship. In her 2022 autobiography Calling the Shots, Sue, who believes Cliff has exaggerated the significance of their time together, wrote: "I begged Cliff to have some respect for my marriage and to stop mentioning me. It would have been so easy for him to say to any inquiring journalist: 'Sue is happily married to Lance now, let's leave it'.
"Twenty years on, I'd still be reading comments from him such as, 'I didn't love her quite enough to marry her', and I'd think: 'He can't be talking about me, surely?' It never got to that level."
She added: "If someone had told me that my relationship with Cliff would last a few months but I'd still be hearing about it 40 years later, I wouldn't have gone near him. Frankly, it looks silly now that he's still talking about a relationship that was never really more than a friendship."
'Ruthless' break-up
Sir Cliff was also previously romantically involved with dancer Jackie Irving, with the pair said to be 'virtually inseparable' for one fateful summer in Blackpool back in the 1960s. Recalling their long-ago seaside romance in his 2020 autobiography Cliff Richard: The Dreamer, Sir Cliff shared: "We hung out all of the time at the shows and in our spare time. Jackie was such a good laugh and, of course, a great person to go dancing with!"
The Mistletoe and Wine singer even considered popping the question to the 'extremely beautiful' 19-year-old Jackie, but quickly realised that an engagement wouldn't fit with his stardom ambitions. During an interview on Piers Morgan's Life Stories in 2020, Sir Cliff revealed: "In the case of Jackie Irving, I went to my manager and said, 'If I got married, would I survive my fans?' He said, 'You might lose 25 to 30 per cent of your fans'. I was like, 'You're kidding! I'd lose one-third?' I broke up with Jackie."
Taken aback, Piers exclaimed, "Seriously?", to which Sir Cliff replied, "I can't make you understand." Piers responded: "No, I'm understanding, I'm just seeing a ruthless... even when you thought you were in love with a woman." Although Cliff remarked that he 'did kiss her goodbye', Piers wasn't convinced, retorting: "Yet the moment you're told by your manager it might cost you a quarter of a third of your fans and success - bang, done! Not even a second thought! It's quite ruthless."
Arguing his case, Sir Cliff hit back: "It just means I wasn't in love enough with her. But just because you can't understand it doesn't make me ruthless."