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HomeTv & ShowSean Penn lunches with Cindy Crawford's husband Rande Gerber

Sean Penn lunches with Cindy Crawford's husband Rande Gerber


Sean Penn was spotted stepping out to lunch this Thursday with Cindy Crawford’s silver fox husband Rande Gerber.

They took the same car to their restaurant of choice, which happened to be Rande’s own Malibu eatery Cafe Habana.

For his latest outing Sean, 61, cut a dashing figure in a black leather jacket over clinging t-shirt that emphasized his burly figure. 

Out and about: Sean Penn was spotted stepping out to lunch this Thursday with Cindy Crawford's silver fox husband Rande Gerber

Out and about: Sean Penn was spotted stepping out to lunch this Thursday with Cindy Crawford’s silver fox husband Rande Gerber

Rande, who famously co-founded the tequila brand Casamigos with George Clooney and Mike Meldman, teamed a grey jacket with a matching top.

The silver fox has been married to Cindy since 1998 and shares two children with her -Kaia, 20, and Presley, 22, who have both gone into modeling.

Meanwhile last month Sean finalized his divorce from his latest wife Leila George, who at 30 is younger than his daughter Dylan Penn.

Leila’s mother Greta Scacchi is only six months older than her ex-husband, while her father Vincent D’Onofrio is only a year older than Sean.

Movie star: For his latest outing Sean, 61, cut a dashing figure in a black leather jacket over clinging t-shirt that emphasized his burly figure

Movie star: For his latest outing Sean, 61, cut a dashing figure in a black leather jacket over clinging t-shirt that emphasized his burly figure

Last June, three months before Sean and Leila separated, they were spotted enjoying a double date with Cindy and Rande.

Shortly before the divorce was finalized Sean confessed in an interview with Hollywood Authentic that he was still ‘so in love’ with Leila. 

He admitted to having ‘f***ed up the marriage,’ saying: ‘We were married technically for one year, but for five years, I was a very neglectful guy.’

The Oscar-winning actor clarified: ‘I was not a f***ing cheat or any of that obvious s***, but I allowed myself to think that my place in so many other things was so important, and that included my place in being totally depressed and driven to alcohol and Ambien at 11 o’clock in the morning, by watching the news, by watching the Trump era, by watching it and just despairing.’

By the way: They took the same car to their restaurant of choice, which happened to be Rande's own Malibu eatery Cafe Habana

By the way: They took the same car to their restaurant of choice, which happened to be Rande’s own Malibu eatery Cafe Habana

Sean noted that ‘beautiful, incredibly kind, imaginative, talented young women who get married to a man quite senior to them in years, they don’t actually love it when they get up from their peaceful night’s sleep and their new husband is on the couch, having been up since four, watching all of the crap that’s going on in the world and has decided that 10:30 in the morning is a good time to neck a double vodka tonic and an Ambien and say: “Good morning, honey. I’m going to pass out for a few hours and get away from all this s***.”‘

Rumors circulated at the beginning of August 2020 that Sean and Leila had secretly tied the knot after four years of dating.

News of the wedding spread when they received congratulations on Instagram from Josh Brolin, as well as from movie producer Mike Medavoy’s wife Irena.

The way they were: Last month Sean finalized his divorce from his latest wife Leila George, who at 30 is younger than his daughter Dylan Penn; he and Leila are pictured in March 2020

The way they were: Last month Sean finalized his divorce from his latest wife Leila George, who at 30 is younger than his daughter Dylan Penn; he and Leila are pictured in March 2020

A few days later Sean went on Late Night With Seth Meyers and showed off his gold wedding band, confirming that he has married for a third time.

‘We did a COVID wedding. By that I mean it was a county commissioner on Zoom, and we were at the house,’ Sean revealed. 

Sean had been married twice before, to Madonna from 1985 until 1989 and to Robin Wright, the mother of his two children, from 1996 to 2010. 

Remember when: Sean was previously married to Madonna from 1985 until 1989 and to Robin Wright, the mother of his children, from 1996 to 2010; Sean and Robin are pictured in 2005

Remember when: Sean was previously married to Madonna from 1985 until 1989 and to Robin Wright, the mother of his children, from 1996 to 2010; Sean and Robin are pictured in 2005

‘There is no shame in my saying that we all want to be loved by someone. As I look back over my life in romance, I don’t feel I’ve ever had that,’ he said in 2012.

Sean told Esquire: ‘I have been the only one that was unaware of the fraud in a few of these circumstances blindly. When you get divorced, all the truths that come out, you sit there and you go, What the f*** was I doing? What was I doing believing that this person was invested in this way?’

‘Which is a fantastically strong humiliation in the best sense. It can make somebody very bitter and very hard and closed off, but I find it does the opposite to me.’

Friendly: Sean and Madonna were seen posing amicably with one another while attending a Haitian relief gala he threw in Beverly Hills in 2016

Friendly: Sean and Madonna were seen posing amicably with one another while attending a Haitian relief gala he threw in Beverly Hills in 2016

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