James Bond heartbreak: Sean Connery’s ‘ultimate jilt on traumatic wedding day’

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The Scottish actor’s impressive legacy was honoured last month after he died at the age of 90 following a long battle with dementia. Sir Sean, who played James Bond in seven films, breathed life into Ian Fleming’s legendary British spy and launched the franchise with Dr No in 1962. Sir Sean and Australian actress Diane Cilento were married for 11 years and had one son Jason, now 57. Unearthed accounts reveal that Ms Cilento married the star after several rejected proposals and that their wedding day was far from the happiest day of their lives.

Sir Sean was besotted with the late actress, best-known for her performance in The Third Secret, and after she fell pregnant he had a “difficult task of persuading her to marry him”.

Ms Cilento was sceptical about tying the knot after a difficult first marriage to Italian assistant director Andrea Volpe ended after four years in 1960 – but the James Bond actor was persistent. 

In the 1993 biography Sean Connery: The Untouchable Hero, Michael Feeney Callan claimed the actor’s “desolutory love affairs that filled the vacuum” were gone. 

Instead, they were “suddenly stout-heartedly replaced by a new and vigorous relationship” shortly before the premiere for Dr No. 

Ms Cilento told a US magazine in 1961 that she didn’t think she was “meant to be married” but less than two years later, she had tied the knot to Sir Sean. 

She said: “I didn’t want to get married, having made a bodge of it already, I didn’t rate marriage. I thought it was too stifling.” 

An unnamed friend of the actress revealed: “We waited for the knot to be tied… we waited for a move from Sean anyway, Diane was another kettle of fish. 

“You see, Sean, under it all, was a one-woman man. Diane, well, she had a career to be catching up with.”

The actor introduced Ms Cilento to his parents Effie and Joe, in the Fountainbridge, Edinburgh, and his mother “read between the lines and guessed the seriousness of the affair”. 

Sir Sean finally convinced her to marry him after he purchased a 12-bedroom house for £9,000, approximately £199,500 in today’s money, in Acton, London, and had started work building a nursery.

A friend of the actor said: “Sean was never enamoured of the idea of children but he was anxious about the baby once he knew the die had been cast. 

“And he loved Diane, remember. He told people she reminded him of his mother – bright, strong, firm.”

Days after she accepted Sir Sean’s proposal they were due to get married in Gibraltar – which biographer Mr Callan explained was “simplest for many reasons”.

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In the UK at that time, couple’s had to wait three weeks after registering to get married and the actor feared “unwanted press coverage” after the documents were filed.

Mr Callan claimed Ms Cilento’s past would have left “certain jaundiced circles… abuzz with the scandal”.

He wrote: “A scarlet lady, just one month divorced, seven months’ pregnant and hopping in and out of love with Connery.”

A friend claimed that Ms Cilento had “jilted him a few times” before their wedding day when he tried to arrange the ceremony, which made him “never too sure of her”. 

The most devastating of those rejections, which Mr Callan described as “the ultimate jilt”, came on the day they tied the knot.

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Ms Cilento was staying with friends in Spain and had arranged to meet Sir Sean in Gibraltar to get married – but the day was not to go as planned. 

Mr Callan recalled: “Connery, travelling on his British passport, had no trouble entering the colony but Cilento, with her Australian documents, was delayed at the frontier. 

“The ceremony was postponed for a few hours, new witnesses had to be roped in – two taxi-drivers, for convenience – and, at last vows were exchanged.”

Ms Cilento described that Connery’s “mood was foul” but she found the affair amusing – “like a funny TV show” and that Sir Sean “was all feet, all thumbs, frustrated”.

That night to celebrate, they hiked up the Rock of Gibraltar, known as Jabel-al-Tariq, to watch the sunset over the Mediterranean Sea but they “stayed up too long”. 

During their descent, they strayed into a “military preserve” where they were said to have been “lucky to find a sentry with a sympathetic ear” after an hour of aimless wandering.

Ms Cilento recalled that after they returned to their honeymoon base, The Rock Hotel, they were exhausted and had a “night of anticlimax after the dramas of the day”.

Sir Sean and Ms Cilento were married for 11 years before they divorced in 1973 – the actor would marry artist Micheline Roquebrune two years later, who he remained with until his death. 

Ms Cilento, who died from cancer aged 78, nine years ago, told Sunday People about her doubts for their doomed marriage: “Sean was so sure we could make a go of it. 

“I wanted us both to retain a fair amount of freedom. I don’t like ownership in marriage. I don’t like too many promises either. There is no way of being sure you can keep them.”

Michael Feeney Callan’s 1993 book Sean Connery: The Untouchable Hero was published by Virgin Books and is available here.

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