Plus: Madonna clubs in New York City, Jennifer Lopez and more

By People Staff
Updated October 19, 2010 06:00 AM
Kristian Dowling/PictureGroup

Paris and Nicky Hilton hit the town Friday night for a double date with boyfriends Cy Waits and David Katzenberg. The foursome dined at Hollywood’s Cleo at the Redbury, sharing Mediterranean specialties like Htipiti and baba ganoush dips with flatbreads. Though Paris’s paparazzi-shy boyfriend slipped in and out the side entrance, the camera-ready heiresses arrived at the restaurant’s front door.

Madonna cozied up to a new man Thursday night while partying at Libation hosted by DJ Ian Friday at New York City’s Sullivan Room bar. The pop diva arrived with a group of about 20 people – but only had eyes for her date. “They were very flirty,” says an onlooker. “She was very much up on him and did not leave his side.”

• Before she gets down to business on American Idol, Jennifer Lopez is enjoying a little R&R! The singer and husband Marc Anthony checked into La Concha Resort in San Juan, Puerto Rico, on Saturday, arriving amongst a fleet of six limousines. Though Anthony had a concert that evening, the couple still managed to have some alone time; a source says they were all smiles, and spotted throughout the weekend affectionately passing through the lobby.

Ashlee Simpson-Wentz enjoyed a girls’ night Saturday at Red Rock on Hollywood’s Sunset Blvd. The newly blonde starlet sipped Veuve Clicquot between dances and darts games with friends. “She was really in a great mood and was touchy-feely with her girlfriends,” a witness says. “She honestly couldn’t stop smiling.”

Entourage star Kevin Connolly joined birthday girl Stacy Keibler for her celebration Saturday night at Premiere in L.A. While the two spent a lot of time goofing around “like brother and sister,” according to a source, Connolly still played the part of social butterfly, talking to everyone at the party.