And he wasn't afraid to kiss her in public on the streets on NYC. So who's his new girl?
It's Zoë Kravitz, who's also an actress and daughter of rocker Lenny Kravitz.
Penn and Zoe have been dating for a while, and while we've seen them together on the NYC social scene, this is our first PDA picture.
XOXO, indeed. Someone better send this in to Gossip Girl!
As for Blake? She seems to be doing just fine herself. She got into the spooky Halloween spirit early yesterday when she hit Madame Tussauds New York Dare to Scare Halloween suite at the Renaissance Hotel in Times Square.
"Blake loves Halloween and was in a really great mood," an eyewitness tells me. "She got really into the fun, sipping a 'blood' martini."
The actress was also sporting a brand-new curly hairdo. New guy, new hairstyle?