• 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]