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Sean Penn, 59, and Girlfriend Leila George, 27, Looked ‘Very Much in Love’ at Benefit Gala

Sean Penn GF Leila George, 27, Looked in Love Benefit Gala
Sean Penn and Leila George at ‘Sean Penn Hosts 10th Anniversary Gala Benefiting CORE’ at The Wiltern on January 15, 2020 in Los Angeles, California. Rob Latour/Variety/Shutterstock

Love doesn’t know age! Sean Penn and his girlfriend, Leila George, appeared to be “very much in love” while attending his benefit gala on Wednesday, January 15.

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The 59-year-old Milk actor’s 27-year-old love joined him at the 10th annual gala benefiting CORE, an organization Penn founded that helps communities affected by devastations, at The Wiltern Theatre in Los Angeles. A-list attendees sipped on beverages from Casamigos and enjoyed live performances from Beck and Portugal the Man, among others.

Penn’s girlfriend sat between him and Leonardo DiCaprio, sans girlfriend Camila Morrone, during the auction portion of the evening. George would “occasionally” talk and “laugh” with DiCaprio, an eyewitness tells Us Weekly exclusively. But things between Penn and George “got more affectionate” throughout the night.

“Sean had his arm around her and rubbed her back as she leaned her head on his chest,” the onlooker shares. “They [would] whisper in each other’s ears and laugh.”

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They even shared an “intimate moment,” where George turned to face Penn while seated and stared “deep into his eyes like she wanted to plant a big kiss on him.” George also put her “head close” to Penn’s while “grabbing the back of his head with her fingers through his hair.” They then “put their heads together and smiled, looking “very much in love.”

Stars like Julia Roberts, Patricia Arquette, Naomi Campbell and G-Eazy were also in attendance on Wednesday.

Penn has been dating George since 2016. They were first seen together that October, packing on PDA while enjoying a beach vacation in Hawaii. The Australian actress was 24 at the time. Though they have kept their romance relatively under the radar, George made an appearance in Penn’s 2018 audiobook, Bob Honey Who Just Do Stuff.

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The I Am Sam star was previously married to Madonna from 1985 to 1989 and Robin Wright, with whom he shares daughter Dylan, 28, and son Hopper, 26, from 1996 to 2010.

He last opened up about Madonna, 61, during an appearance on The Late Show With Stephen Colbert in March 2018. In a segment called “Sean Penn-y For Your Thoughts,” he was asked to choose between the “Into the Groove” singer and Britney Spears.

“Ah, I love my first wife very much,” Penn said at the time. “There’s no [comparison] … you don’t compare those things.”

Colbert responded, “People compare them all the time! So you’re going with Madonna?” However, Penn smiled and replied, “Sure.”

With reporting by Taylor Ferber

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