updated 07/28/2010 AT 4:00 PM ET
•originally published 07/29/2010 AT 6:00 AM ET
Leonardo DiCaprio and Charlize Theron were enjoying separate nights out when they saw each other hanging at Teddy’s inside the Hollywood Roosevelt Hotel. The actress and her girlfriend were invited to join the Inception star and his pals at their table. According to an onlooker, the vibe was polite and sweet, and Theron introduced herself to the table with handshakes and hellos. Conversation flowed and everyone laughed, seemingly having a great time. Theron snuck out before other guests, though not before giving DiCaprio a hug goodbye.
Penn Badgley, grabbing a sweet snack at Billy’s Bakery in New York. The Gossip guy stopped into the Chelsea location solo and ate a red velvet cupcake and drank skim milk while waiting to pick up his order, which included a large cake and a dozen cupcakes.
Is he becoming a regular? After dining at Hub 51 with wife Fergie during his last visit to the Windy City, Josh Duhamel stopped into the Chicago hotspot again, ordering a tuna Thai basil roll as he watched sports in the bar. The actor, in a hat, remained incognito and went unnoticed by fans.
Newly single Mark-Paul Gosselaar and buddy Breckin Meyer, hanging out and working on their golf game during a visit to the Resort at Pelican Hill in Newport Coast, Calif.
Donald Trump, stopping Chelsea Handler to compliment her on her late-night talk show and asking to be booked as a guest during a party for Chelsea Lately regular Heather McDonald’s book, You’ll Never Blue Ball in This Town Again at Boa Steakhouse in L.A. Also there: Kris Jenner.
By DAVID CAPLAN, PAUL CHI and JENNIFER GARCIA