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Couples Watch: Rihanna & Chris, Ashlee & Pete

10/06/2008 at 06:00 AM EDT

Couples Watch: Rihanna & Chris, Ashlee & Pete
Chris Brown and Rihanna
Kevin Mazur/WireImage

Chris Brown

Chris Brown

Rihanna

Rihanna

• Undercover lovebirds Rihanna and Chris Brown, starting their exciting night on the town with dinner at Giorgio Baldi in Santa Monica. Then, the two popped into the Hideout, a small bar next door. "They came in with their bodyguard and watched people getting up to sing karaoke," says an onlooker. "They were laughing hysterically –not at everyone, but they just thought it was so cute and funny." Alas, neither pop star took turns on the mic. After getting their fill, the two left, holding hands on the way out the door.

Hilary Duff, celebrating her 21st birthday – actual date: Sept. 28 – at New York's Bagatelle with boyfriend Mike Comrie and friends. The pop star and her pals shared appetizers and leek ravioli, and the birthday gal was "very low-key and super sweet." Among their beverage purchases: two bottles of Lokoya wine, priced at more than $400 each. Their total bill was more than $2,500.

Ashlee Simpson-Wentz, eating a late dinner with husband Pete Wentz at David Burke's Primehouse inside Chicago's The James Hotel. The couple was joined by Wentz's father and friends. Simpson ordered a well-done steak and acted very "lovey dovey" with her husband. Before their dinner, the pair were spotted sitting in the front row during the opening night of Chicago Fashion Focus, an event that Wentz hosted.

Lauren Conrad and Kyle Howard, making their weekly pilgrimage to jazz night at Teddy's inside the Hollywood Roosevelt Hotel. The Hills star pulled Howard and another friend in a line, hand-in-hand, toward the bathroom before returning to the bar. According to an onlooker, the two disappeared for some time, then returned to the bar, where they seemed to be closing their tab. As they paid, Howard grabbed a cherry from a cup on the bar, and Conrad stole an olive. Meanwhile, the two never stopped smiling at each other – and Howard had his hand on her shoulder.

Sean Penn and Robin Wright Penn, looking very much in love at New York's 21 Club after the Manhattan premiere of their new Hollywood satire, What Just Happened. "They were very tender toward each other," says one partygoer. "They were holding hands. They seemed really happy."

Also Spotted ...


Catherine Zeta-Jones and Michael Douglas, sharing a romantic lunch at New York’s Ocean Grill, where they split the Seafood Castle and sipped on several glasses of Chardonnay. ... David Schwimmer and British girlfriend Zoe Buckman, dining with the cast of Fault Lines, the new play he's directing on Broadway at Commerce restaurant in New York City’s West Village. At the star-studded dinner, the two "never left each other's side."

• By K.C. BAKER, JENNIFER GARCIA, KRISTEN MASCIA, LESLEY MESSER, KIM PEIFFER and ABBY STERN

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