Rihanna Having Secret Dates on City Rooftops

Narciso Rodriguez rescued Claire Danes’s dress when a CFDA Fashion Awards partygoer stepped on its train. Meanwhile Blake Lively hung out with Bradley Cooper, and Justin Timberlake (sans Jessica Biel) hugged Anna Wintour. Rihanna is trying to “be discreet” with her new man, hip-hop artist Drake, hitting up Year One’s after-party on the Empire Hotel rooftop and the VIP area of Greenhouse. Meanwhile Kanye is directing Drake’s “Best I Ever Had” video in Brooklyn, and was also the target of a bad Chris Brown joke at Caroline’s on Broadway. Lindsay Lohan and Samantha Ronson broke up again (yawn), but this time it was because Nicole Richie told Ronson not to bring LiLo to her party, so she didn’t, then Ronson had dinner with Richie and dumped LiLo via text. We’ll see how long this lasts.

Will and Jada Pinkett Smith were giggly over dinner at Bar Masa, probably because they just got it on in one of their friends’ bathrooms, which they like to do from time to time. Judd Apatow tells Playboy that he’s bad in bed. And not in the good way. Whitney Port partied with her latest City cohorts at East Hampton’s Lily Pond, whom MTV brought on the show “because the first season was so boring and because Olivia Palermo now works at Elle and can’t be out going wild.” A recently single Countess LuAnn de Lesseps downed tequila and flirted with twentysomethings at the Georgica over the weekend, which is exactly what she did last weekend. Michelle Pfeiffer doesn’t want to be called a cougar.

Mal Sirrah designer Malcolm Harris hung up on Angelina Jolie twice when she called to order three of his dresses, not believing the A-lister would actually give him a ring. Andrea Bocelli serenaded Mario Cuomo for his 77th birthday, then headed off to Le Cirque with Sirio Maccioni, Martha Stewart, and Pamela Fiore. Barry Diller was hanging out at the Manhattan Supreme Court for jury duty. Ed Norton, who partied with Diane Von Furstenberg, Molly Sims, and Gerard Butler at Calvin Klein’s CFDA bash at the High Line, used to smoke weed on Horatio Street and only supported the High Line because he never really thought it would succeed. Some model fell into a bubble bath at Chris Coffee’s Cooper Square Hotel party.

Much to our disappointment, Christopher Mintz-Plasse (a.k.a. McLovin) reports that there’s no Superbad sequel in the works. Melissa Joan Hart, who just gushed about her weight loss on the cover of People, shared crêpes, chocolate cake, and a chocolate pizza with her family at Max Brenner. Owen Wilson says he’s over Kate Hudson. Except that he’s dating her twin. Megan Fox hates little kids who try to give her flowers. And Amy Winehouse’s parents (who look surprisingly normal?) think her drinking could be a problem. Nice to know they’re on the ball with that one.

Rihanna Having Secret Dates on City Rooftops