Will Tom Cruise Ever Find Lasting Love? The Hollywood Bachelor’s Quest Continues.

There was an inevitability about it, a sense of deja vu perhaps, a feeling that this familiar ground, a predictable journey we’ve all been on before – albeit as objective spectators. 

Indeed, as of Wednesday evening Tom Cruise is officially single – and back among the most eligible bachelors in Hollywood – after his latest high profile relationship, with Cuban-American actress Ana de Armas, came to an abrupt end. 

We’ve been here before, of course, and only the more optimistic of fans might have expected more from the veteran star’s romance with a woman some 27-years his junior.  

After all, the tropes that define so many of his failed romances – the younger co-star, the sporadic joint appearances, the almost non-existent public displays of affection – were all present and correct long before the death knell was inevitably sounded this week. 

With all that in mind, it does rather beg the question… will Thomas Cruise Mapother IV ever find lasting love at the lofty age of 63? Or is it too late? 

Who knows, but you could forgive him for being reluctant to marry, having previously tried and failed on three different occasions – starting in 1987, when the youthful Cruise, then a promising young actor, exchanged vows with the older Mimi Rogers. 

Having impressed in cult ’80s films The Outsiders, Risky Business and The Colour Of Money, Cruise was already viewed as a desirable romantic prospect – both and off the big screen – as pop legend Cher would later testify. 

The pair embarked on a brief but ‘hot and heavy’ age-gap romance – she was 39, while Cruise was 23 – after meeting at a White House event in 1985 to raise awareness for dyslexia, shortly before his relationship with Rogers. 

Recalling the affair, Cher told Event magazine in 2018: ‘A bunch of people who were dyslexic were invited to the White House, and Tom and I are both dyslexic.

‘We didn’t go out till way later, but there definitely was a connection there.’

It was Rogers, six years his senior and a successful Hollywood star in her own right, who introduced the actor to Scientology, but even his willingness to fully embrace the unorthodox religion wouldn’t save their marriage. 

Just two years after exchanging vows in Bedford, New York, it was over, with Rogers getting a reported $4million payout from the divorce when it was finalised in 1990.

The actress would eventually find lasting love with film producer Chris Ciaffa, her third husband and father to her two children 

Bizarrely, she later claimed it was Cruise’s alleged interest in following a devout spiritual path affected their sex life, and ultimately led to a separation.  

‘Tom was seriously thinking of becoming a monk,’ she told Playboy in 1993. ‘At least for that period of time, it looked as though marriage wouldn’t fit into his overall spiritual needs. 

‘And he thought he had to be celibate to maintain the purity of his instrument. My own instrument needed tuning.’ 

Rogers subsequently retracted the comments, claiming she had been quoted out of context, but admitted being married to Cruise at a time when he was Hollywood’s hottest property affected her own career. 

‘Nobody hires you because you’re married to somebody famous. In fact, I think you’re tested a little extra because of it,’ she said. 

‘You cease to be an individual. Every article was about “Tom Cruise’s wife.”‘ 

Cruise, of course, had already moved on. As the ink dried on his 1990 divorce papers the actor was involved in a new relationship, this time with Australian actress Nicole Kidman. 

Cast as his love interest in director Tony Scott’s Days Of Thunder – think Top Gun on wheels – Kidman soon found herself in an altogether different role, as her co-star’s real life second wife.

The pair sealed their whirlwind romance by marrying on Christmas Eve 1990, and Kidman – 23 on her wedding day – later told the Evening Standard: ‘I was a baby when I married Tom, but I don’t regret any of it.’ 

She and Cruise would adopt two children, Isabella in 1992 and Connor in 1995, while establishing a strong personal and professional relationship, with Kidman also starring alongside her husband in Western epic Far And Away and Stanley Kubrick’s notorious erotic thriller, Eyes Wide Shut. 

But in 2001 the drama was restricted to a Los Angeles courthouse after Cruise effectively ended their 10-year marriage by filing for divorce, citing ‘irreconcilable differences’ as a primary reason for the split. 

Who can forget that famous image of a rejoiceful Kidman, her trademark ginger curls tied into a neat bun, raising her hands to the air as she exited her lawyer’s office following the finalisation of their divorce. 

She would of course enjoy longer and arguably more successful marriage with country star Keith Urban before confirming their separation after 19-years of marriage and two children, in September. 

As history tells us, Cruise would marry for a third and final time with Katie Holmes in 2006, but not before embarking on a short-lived romance with Spanish actress Penélope Cruz, his co-star in 2001 thriller Vanilla Sky. 

It would see a recurring theme emerge in the actor’s love life, notably his predilection for dating co-stars, but Cruise later insisted he only ever fell for them once the job was done. 

He told The Telegraph: ‘I’ve never fallen in love with someone I’m working with. It’s always been afterwards.’ 

In a subsequent 2003 interview with Marie Claire, the notoriously private actor revealed the ‘little things’ he liked to do for the Spanish beauty.

He said: ‘She’ll come home, and I’ll have her favorite kind of food made, have a bath drawn. I like doing stuff like that. 

‘She likes my food, so I cook for her. It’s always the little things I like in a relationship.’

But marriage was clearly off the menu, with Cruise and Cruz – now happily married to fellow actor Javier Bardem – ending the romance in 2004. 

Enter Katie Holmes stage right, and fans would be forgiven for assuming Cruise had finally found the one while discussing their relationship during a now notorious appearance on The Oprah Winfrey show. 

During what transpired to be a toe-curlingly embarrassing exchange, the Hollywood star responded to Winfrey asking him if he was in love by jumping up and down on her sofa, falling to his knees and fist pumping the air. 

Worryingly, Cruise was in his early forties and old enough to know better, while Holmes was 27 and at the top end of a promising career after becoming a household name through US teen drama Dawson’s Creek. 

A breathtakingly romantic wedding followed in November 2006, in the grounds of the 15th-century Odescalchi Castle near Rome, seven months after the birth of the couple’s only child, daughter Suri.

But six years later the writing was on the proverbial wall and a bitter tug-of-war over the former couple’s young daughter would ensue. 

In 2012, Cruise said he was ‘deeply saddened’ that his younger wife Katie had filed for a separation.

He revealed the former Dawson’s Creek actress had initiated the split, bringing a dramatic end to one of Hollywood’s most high-profile romances.

‘This is a personal and private matter for Katie and her family,’ Holmes’s lawyer Jonathan Wolfe said in a statement to PEOPLE magazine at the time.

‘Katie’s primary concern remains, as it always has been, her daughter’s best interest.’

A spokesperson for Cruise, who was at the time in Iceland filming science fiction epic Oblivion, said: ‘Kate has filed for divorce and Tom is deeply saddened and is concentrating on his three children.’

Insiders later claimed the actress ended her marriage to Cruise because she feared she would end up like Kidman – with a daughter who Scientology turned against her.  

In an exclusive interview with Daily Mail in 2016, the father of church leader David Miscavige said Holmes feared Suri could end up cutting off all contact with her under Scientology’s ‘disconnection’ policy. 

‘It’s a toxic policy that ruins lives,’ said Ron Miscavige, whose scathing memoir about his son, Ruthless, was published earlier that year. ‘Katie just didn’t want that to happen so she left.’

Miscavige claimed members of the church’s staff, known as Sea Org, moved in with Cruise and Holmes, to make sure the church’s most valuable celebrity was being properly taken care of.

‘That didn’t sit so well with Katie, of course, and it hurt the marriage,’ he told Daily Mail. ‘She and Tom had big differences about the way life should be lived.’

But the biggest issue was Holmes’s fear that Suri might one day ‘disconnect’ from her if they continued to raise her as a Scientologist and if Katie ever fell foul of or leave the church.

‘The big issue really was raising Suri as a Scientologist,’ Miscavige said. ‘If that happened, some day it was a possibility that she would disconnect from Katie.

‘Ultimately this is what has happened to me.’

Indeed, Kidman’s adopted daughter with Cruise – herself a practicing Scientologist – didn’t even invite her to her 2015 wedding in London – even though the actress was appearing on stage in the British capital at the time. 

So what now for Cruise? The ensuing years have seen him embark on a series of romances, notably with his Mission: Impossible co-star Hayley Atwell, but none have managed to last. 

His stop-start two-year romance with Atwell, 43 and almost 20 years his junior, would officially end in 2022, when a source told The Sun: ‘Unfortunately it hasn’t worked out for them. They have now decided they are better as friends.’ 

The insider also revealed that the fanfare around the couple, who had reconciled only months earlier following an earlier split, was ultimately too much to handle.

‘They get on really well, and have fantastic chemistry, which is why they decided to quietly give the relationship another try earlier this year. 

‘What was working behind closed doors didn’t work out so well when it was made public, and the fanfare around them as a couple exploded again.’ 

Atwell is now happily settled into married life with husband Ned Wolfgang Kelly, while Cruise returns to the dating pool following the collapse of another short lived romance. 

Is true love really Mission: Impossible for the Hollywood star? Watch this space.