“I’d been stagnant,” she says, gazing out the window. Then, spotting a couple making out on the sidewalk, she emits a sound like a low growl. “Oh yeah, get it!” she whoops at them, then nods her approval as they move on, snogging their way up the street. “Isn’t that great?” she grins, then returns to the question at hand. “I think I fucked myself by not being strong enough. It’s almost like waffling—you know, ‘Can I do this? Could I do it completely, with conviction, and be successful?’ I think that’s being young and finding out who you are, and all of a sudden, post-40, you just go, ‘I do know.’ I have the answer; there’s not as much questioning of my abilities.”
Her newfound confidence coincides with big family changes. Unlike many actresses her age who’ve recently had IVF twins, Wright Penn is contemplating an empty nest. Daughter Dylan Frances, 18, is off to college in the fall, and her 16-year-old son, Hopper Jack (named for family friends Dennis Hopper and Jack Nicholson), isn’t far behind. “At least twice a week, I pull over and sob,” says the actress, her eyes welling. “My baby is leaving. It’s an emotionally full time, but it’s not sad. I can’t wait for Dylan to go [out and] live. That’s what makes me cry.” With the duties of motherhood lightening, she says, “I feel younger than I ever have.”
And less private. After years of protecting herself and her family from the spotlight, Wright Penn is now signaling that she’s ready for her close-up. At the Cannes Film Festival in May, for example, she was an arresting presence, strolling the red carpet as a member of the jury. “There’s clarity of life now,” she says. “I think I’ve always been a follow-the- leader with my career, or maybe waiting for things to happen. Now I’m like, ‘I’m OK—I know the direction, whoever’s on board can go with me.’ ”
Unspoken but clear is that Sean Penn may not be on that train. Even before their marriage in 1996, the couple rollercoastered through years of ups and downs. They split after each of their children was born (in 1991 and 1993). In December 2007, each filed for divorce, citing irreconcilable differences, then withdrew their petitions four months later. Wright Penn was prominently by her husband’s side at this year’s Academy Awards, where Sean won best actor for Milk. But two months later, he filed for a legal separation. Then, while Wright Penn was in Cannes, he withdrew his filing, calling it an “arrogant mistake,” and later dropped out of two films to reportedly focus on his family. At press time, despite media speculation to the contrary, the couple was separated and Wright Penn had no plans to reconcile.
Even friends of the couple are at a loss to describe what one calls their “peculiar chemistry.” There are signs that Sean’s greater celebrity was hard for Robin to deal with. “She always referred to herself in the fame area as ‘Sean Penn’s wife,’ ” says another friend. “She said, ‘People never look at me and say, “There’s Robin Wright Penn.” They’re just looking at me because I’m Sean Penn’s wife.’ ” Asked about her marriage, Wright Penn tosses her hair and looks out the window before saying that she’s ready to move on. “I hit that crossroad a while ago— for Robin [ jabbing her hand at herself], the ‘I know what I don’t want’ was flashing neon lights,” she says. “I have no regrets. I, we, have two amazing children we raised together.”