Sean Penn, aged 65, and his significantly younger girlfriend, Valeria Nikoff, 30, enjoyed a shopping trip post-Golden Globes.
On Wednesday, the couple was spotted holding hands in Santa Monica, California. Penn was seen engaging in conversation with Nikoff, who seemed to be quite cheerful during their outing. Interestingly, Penn had a cigarette in his other hand, which caught the attention of onlookers.
Penn dressed casually in a white button-up shirt paired with a blue blazer and black trousers. Nikoff chose a stylish all-black look, featuring a sweater, slacks, and a coat, complemented by sunglasses and a shoulder bag.
This outing followed Penn’s appearance at the 2026 Golden Globe Awards, where he was photographed lighting up. He was notably seen sitting next to Leonardo DiCaprio, with several cigarettes seen in a glass cup on the table nearby.
At the Golden Globes, Penn was nominated for Best Supporting Actor for his role in the Paul Thomas Anderson film, *One Battle After Another*. Other nominees in that category included Benicio del Toro, Jacob Elordi, Adam Sandler, Paul Mescal, with Stellan Skarsgård ultimately taking home the award. Despite his nomination, Penn did not attend the ceremony with Nikoff.
The couple, who have been dating since September 2024, marked their red carpet debut at the Marrakech International Film Festival in November of that year. Penn’s romantic history includes marriages to Madonna from 1985 to 1989, Robin Wright from 1996 to 2010, and Leila George from 2020 to 2022.
