09/02/2008 AT 06:00 AM EDT
, hanging alfresco at West Hollywood's Chateau Marmont. The starlet took a patio table with a male friend, laughing and enjoying her pal's company. Olsen, who sported her signature plaid, smoked several cigarettes while outside – then called it an early evening.
Also at the Chateau: Nicole Richie
, who wandered the courtyard looking for her friends. The new mom whipped out her phone but noticed her party right away, and put away her cell. Meanwhile, Joel Madden
was sitting at the table, wearing a baseball cap and eating. Richie, who arrived with another male friend, sat one seat away from her beau, and leaned in to chat with her friends at the circular table. And at a separate patio table: Garth Brooks
, in a red button-down shirt and jeans, shared a business dinner with two males.
, dining at Blackbird, a trendy restaurant in Chicago's West Loop, with her celebrity chef pal (and PBS cohost
) Mario Batali
and another couple. The actress sat on the patio, a source tells us, and was so under the radar that few diners even noticed her.
Celebrity chef Gordon Ramsay
, buying a tuxedo at Paul Smith in West Hollywood. While the chef is known for his fiery temper, an onlooker tells us that he was very nice to the staff as he tried on the tuxedo sans shoes.
Following her win at the U.S. Open, Venus Williams
hit an H&M store in midtown Manhattan but left empty-handed – except for the muscular, bald gentleman who held her hand as they left the store. Once outside, the tennis pro graciously posed for pictures with excited teenage fans.
Following their concert in Milwaukee, the entire Maroon 5
gang hung out at The James, a boutique hotel in Chicago. The band camped out in the hotel's JBar before lead singer Adam Levine
retreated to the hotel's penthouse.
By JESSICA GOLD HARALSON, MARLA LEHNER, MELISSA LIEBLING-GOLDBERG and KIM PEIFFERMonday's Couples Watch >