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Sean Connery's colorful love life: From Diane Cilento to Jill St John and Lana Wood, all the gorgeous women he wooed

The ‘Diamonds Are Forever’ actor serenaded many Bond girls on screen and was known for his casanova image off-screen too
Sean Connery and Jill St John (Getty Images)
Sean Connery and Jill St John (Getty Images)

Flamboyant, charismatic and debonair...Sean Connery is fondly remembered for his magic on the big screen as the first James Bond. Once dubbed the “Sexiest Man of the Century,” the actor died peacefully in his sleep in the Bahamas at the age of 90 after a long illness.

Along with a string of seven back-to-back 007 thrillers, he is also credited for movies like ‘Highlander’ (1986), ‘Indiana Jones and the Last Crusade’ (1989), ‘The Hunt for Red October’ (1990) and ‘Dragonheart’ (1996). With an Academy Award, two BAFTA Awards and three Golden Globes, including the Cecil B. DeMille Award and a Henrietta Award to his credit, he was a living legend. 

Not just his stellar performances Connery was also known for his colorful love life. The ‘Diamonds Are Forever’ actor serenaded many Bond girls on screen and was known for his casanova image off-screen too. Here's a glimpse at all the gorgeous women he dated in real life. 

Sean Connery (Getty Images)

Carol Sopel

A “dark-haired beauty with a ballerina's figure", Carol Sopel was known to be arm candy for Sean Connery. Reports say the actor dated her during the production of ‘South Pacific’ in the mid-1950s but her Jewish family soon shooed him away. He was madly in love with her, and in fact, asked her to marry him. However, Carol's parents saw him and said, “He's just a chorus boy. He's a nothing, a nobody.” The relationship soon fizzled out after Carol turned him down.

Julie Hamilton 

The daughter of documentary-filmmaker and feminist Jill Craigie, Julie Hamilton was said to be romantically involved with Sean Connery for a long time. She was his live-in girlfriend for almost a year, but did you know she wasn't even attracted to him at first? “I didn't like him at first. I thought he was a yob and a terrible bore,” she said but after their paths crossed many times, she found him to be a “gentle, sweet guy”. She said, “He was very old-fashioned. Once I was his lady, that was it. We went everywhere together.”

So, how did the relationship end? One day, the young photographer awoke beside him in bed and he sighed: “What incredible eyes Diane [Cilento] — his stunning Australian co-star in ‘Anna Christie’ and his first wife — has got.” She recalled, “I jumped out of bed and asked him: 'Don't you love me any more?'” Not one to bite his lips, Connery “looked straight back” at her and said, “'No, not the way I used to'.” Hamilton then confessed, “My heart was breaking, but I summoned the courage to gather my things and walk out. I went to my parents' home and cried for days.”

Sean Connery (Getty Images)

Maxine Daniels

Obsessed with the jazz singer, Connery first locked eyes with Maxine Daniels at the Empire Theatre. He tried to win her heart but she made it clear to him she was happily settled with a husband and baby daughter.

Diane Cilento 

The Australian beauty starred opposite Sean Connery in ‘Anna Christie’ (1923) and doubled for her husband's co-star Mie Hama in ‘You Only Live Twice’ (1967). Best known for her role in ‘Tom Jones’ that clinched her an Oscar nomination, she exchanged vows with Connery in 1962. Among one of the high-profile married couples in the film industry the two went their separate ways in 1971 and were divorced two years later in 1973. 

Years later in her 2006 autobiography, she opened up about how he had verbally and physically abused her during their relationship. At that time, he was reported to have said hitting a woman was “no big deal, especially if she is a bitch, or hysterical, or bloody-minded continually”. During the period they were married, Cilento's career saw a steep decline. The couple had one son, Jason Connery. 

Sean Connery and Diane Cilento (Getty Images)

Jill St John

Jill St John is best known for her role as diamond smuggler Tiffany Case, the love interest of James Bond in ‘Diamonds Are Forever’ (1971), where she starred opposite Sean Connery. The two were reportedly dating each other. At the time, Connery was said to have separated from his then-wife Diane Cilento even though they were not formally divorced.

Lana Wood

Former Bond girl Lana Wood opened up about her Sean Connery affair in a Daily Mail interview. Talking about how he made the first move, she said, “I was never that forward. We went out to dinner, then met some of his friends, then went for a walk, and you know. We actually started having an affair before filming began, but we kept it secret.”

The younger sister of actress Natalie Wood played Plenty O’Toole in ‘Diamonds Are Forever’ (1971). “Neither of us was married at the time, but it still isn't done to be public about it. I remember being very embarrassed when we had to do the love scenes because we were trying not to let people know. You want to be a good actress, but for it not to seem too convincing.”

Sean Connery and Lana Wood (Getty Images)

Carole Mallory

Carole Mallory was first introduced to James Bond star Sean Connery at a dinner meeting suggested by a producer friend on a visit to Manhattan. Shedding light on the night, Daily Mail reports, “Perhaps inevitably, the Scottish actor wheedled an invite back to Carole's.” Mulling over old times, she said, “We saw each other a few times, but he was married and I hated having to sneak around... The affair fizzled out. Sean had no respect for women, but at least I got a meal on him.”

Shockingly, in the same interview, she also called him “one of the worst” in bed. When asked who was her best lover, her blue eyes flashed cheekily but she rebuffed the question. “I'd hate to hurt anyone's feelings by saying who was the best,” she said, adding, “You can't do that to men. They're so insecure. But I'll tell you who was the worst in bed. It was Sean Connery. Let's just say he didn't leave a very big impression.”

Magda Konopka

Polish model and actress Magda Konopka was also romantically linked with Sean Connery for a short period. A few reports alleged that she flirted and spent some nights with Sean Connery in Porto Rotondo. 

Sean and Micheline Connery (Getty Images)

Lynsey de Paul

Think of Lynsey de Paul and a picture of the fiercely independent sexy pop star pops up. Known for her string of hits like ‘Sugar Me’ and ‘Won't Somebody Dance With Me’ in the ’70s, she opened up about her adulterous affair with Sean Connery in a documentary. “I wasn't aware of Sean's violent side when I was with him, but I was quite horrified when I read that he had said it was OK to hit a woman. And if what Diane said wasn't true, then why has he never denied it?” she said.

“I didn't want to have an affair with him and I tried to keep our relationship platonic but he pursued me relentlessly. He wasn't my type at all because I'm not usually attracted to the macho type. At the time I didn't detect his violent side. All I saw was this charming man who quoted Robbie Burns, wrote his own poetry and had even written a ballet. I'm a sucker for all that. In the end I thought: 'Why not?' I didn't know his wife so I didn't feel I was betraying her by having an affair.” Recalling how it ended abruptly, she said, “I was a stupid girl to become involved with him. I don't think I was in love with him — I was just flattered by the full-on attention.”

Micheline Roquebrune

Married for 45 years the couple first crossed paths at a sporting event in Casablanca, Morocco. The two exchanged vows in 1975 and were seen at a number of red carpet events celebrating milestones as a couple. In his last days, he seemed to be enjoying his life with his partner. “I’ve had a great career and I suppose I am in retirement,” he said in an interview.