The List on MSN

Sean Penn's massive age gap with his girlfriend beats Karoline Leavitt & her husband

There are a whopping 32 years between White House Press Secretary Karoline Leavitt and her husband, but Sean Penn and his ...

Sean Penn, 65, Steps Out With 30-Year-Old Girlfriend Valeria Nicov in Santa Monica After Scandal

Sean Penn was photographed in Santa Monica with girlfriend Valeria Nicov, marking their latest public appearance amid recent awards-season attention. Sean Penn, 65, and Valeria Nicov, 30, were seen ...

Madonna reportedly 'shocked' by ex Sean Penn's natural aging: 'She's not used to that reality'

Famous singer Madonna is reportedly taken aback by her ex-husband, Hollywood star Sean Penn's, natural agin ...
Page Six

Sean Penn, 65, and much-younger girlfriend, 30, hold hands on rare public outing after Golden Globes

Sean Penn and his much-younger girlfriend, Valeria Nicov, stepped out for a shopping date after the Golden Globes. The “Mystic River” star, 65, and the actress, 30, were photographed holding hands ...

Madonna ‘Appalled’ By Ex-Husband Sean Penn’s Aged Appearance: ‘Shock to Her System’

It’s been more than 40 years since Madonna married Sean Penn — and he’s changed a lot. The pop icon, 67, was “appalled” when she saw her ex-husband recently, Rob Shuter reported in his Naughty But ...
E!

Sean Penn Steps Out for Rare Date With Girlfriend Valeria Nicov After Golden Globes

Sean Penn is having one outing after another. Three days after he attended the 2026 Golden Globes, the two-time Oscar winner enjoyed a low-key date in Santa Monica, Calif., with girlfriend Valeria ...