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Rosie O'Donnell told Howard Stern yesterday that she "had a chance to romance" Angelina Jolie back when they were both single and they talked on the phone a few times, but they never ended going out for dinner as planned, alas. She also says Petra Nemcova once sent her "love signals" when the model was a guest on Rosie's talk show, but she didn't capitalize on that opportunity either. Rosie has a new satellite radio show launching next week, so don't be surprised if more of these missed love connections surface in the coming days. [NYDN, CM]
• In other creepy celebrity sex news, a new book by controversial biographer Andrew Morton claims that Angelina Jolie slept with her mother's live-in boyfriend when she was 16 years old. And a second Jolie tell-all, to be published on December 1, claims Angie once contemplated suicide, has a history of heroin use, and, when it comes to her relationship with Brad Pitt, has "successfully manipulated the public into believing a glamorous fairytale that bears little resemblance to the reality of the pair's life together." [DM, Us]
• Ashley Dupre popped by Scores last Saturday night. She didn't strip, but she did make out with her new boyfriend PJ all night, so patrons of the strip club didn't go home totally empty-handed. [P6]

• As Nobu boss Richie Notar will attest, taking sleeping pills and drinking alcohol when you get on a flight is never a good idea. [P6]
• During the first preview of Matthew Broderick's new play, "The Starry Messenger," the actor had to stop the play several times to ask for his lines, which made everyone in the audience "feel awkward." Now the producers have pushed the opening back a week, which is also awkward. [NYDN]
• Ever since Lindsay Lohan's Hollywood Hills home was robbed, the manse has felt "tainted" to her, so now she's moved into a West Hollywood condo with tight security. But if the world now knows that nobody's living in her house, won't it just get robbed again? Oops. [P6]
• The Michael Jackson documentary, This Is It, premiered last night in 16 cities around the world. Gayle King, Ice-T, Russell Simmons, and Sherri Sheppard turned out for the New York premiere; Jennifer Lopez, Will Smith, and Paris Hilton showed up in Los Angeles. [NYDN]
• Michael Lohan is talking again. He told Grazia magazine that he's worried his daughter "could be dead in a year." Then he went on Maury Povich to say he was going to "save her life" even though he hated to "speak out publicly like this." Still no word on exactly how he plans to save her, though, since LiLo is still ignoring him. [NYDN, TMZ]
• In his new autobiography, Andre Agassi admits that he used crystal meth regularly in the late '90s and then lied about it when he tested positive for drug use. But he opens up about his hair loss and relationship with Brooke Shields, too, so clearly there's a little something for everyone. [People, NYP]
• Arnold Klein, Michael Jackson's plastic surgeon and favorite prescription-writer, performed 170 procedures on Jackson in the last three months of his life. He'd now like to get paid for his services, so he's filed a creditor's claim against the Jackson estate. [TMZ]
• A company that helped produced Naomi Campbell's perfumes has filed a lawsuit against the supermodel for breach of contract after she allegedly stopped paying them their quarterly cut of profits. [NYP, NYDN]
• When Tim McGraw asked New York real estate maven Barbara Corcoran if she had any real estate to sell him in the Today show green room, she responded with, "Nope, you can't afford it," since she didn't know who he was. Awkward! [P6]
• Jessica Simpson is in India filming her show The Price of Beauty, and she's been spotted sporting a henna tattoo and a bindi. Just so you know. [DM]
• Ryan Seacrest is producing a new E! show called The Bank of Hollywood in which contestants will pitch a "money-making idea to business leaders." Candy Spelling will be a judge on the program for some reason. [P6]
• Dane Cook wasn't fazed by complaints from other tenants in his apartment complex last year that he didn't pick up his dog's poop because he thinks it keeps him "from being vanilla," he said. Well, that, or it just makes you a disrespectful pig. [P6]
Ivana Trump brought her matchmaker with her to Ivanka's wedding last weekend for some reason. [P6]
• The Jonas Brothers are not breaking up, even though Nick is starting a band on the side and Kevin is getting married. So feel free to tell your niece to stop with the crying. [People]
• Lisa Kudrow will make a guest appearance on Courteney Cox Arquette's show Cougar Town. Cox Arquette apparently also asked Matthew Perry to be on the show, but he turned her down. Clearly, it was all those other huge roles he's so busy with. [TVGuide]