Cityfile: New York's Most Notable and Influential

• In what may be the weirdest celebrity extortion attempt ever, a German male model named Edis Kayalar has been arrested for trying to blackmail Cindy Crawford and her husband Rande Gerber with a "sexy" photo of the couple's then 7-year-old daughter "in revealing clothing, bound to a chair and gagged." Apparently, the pic had been taking by the girl's former babysitter during an innocent game of cops and robbers and she used to date Kayalar. [NYDN, People]
• All those phone calls that Michael Lohan recorded may ultimately land him in jail (again). A 2005 protective order obtained by Dina Lohan banned him from communicating with her by email or phone until 2011. [TMZ]
• Spend enough time on Twitter and you, too, may find yourself dating a beautiful young starlet! Emmy Rossum says her relationship with Counting Crows singer Adam Duritz "began with a Tweet," believe it or not. [People]More

• Was Lindsay Lohan dating Heath Ledger at the time of his death? That was what came out yesterday when the latest clip from Michael Lohan's vast archive of recorded phone conversations was posted online. (Dina Lohan can be heard expressing concern that Lindsay was headed down the same path.) On tap for today? A call between Dina and Michael in which she tells her ex-husband that Lindsay has been cutting herself. [NYDN, NYP, Radar]
• Alleged David Letterman extortionist Robert "Joe" Halderman appeared in court yesterday where his lawyer asked a judge to drop all the charges against the former news producer. The reason? Halderman's $2 million demand wasn't blackmail, silly. It was a legitimate business proposal in which Letterman could have first dibs on his screenplay, naturally. [NYP, NYDN, TMZ]
• Rihanna says she put on the tightest dress she could find to pick up Glamour's Woman of the Year award on Monday night at Carnegie Hall. She also spent $50,000 flying in her mom, aunts and brothers from Barbados to join her at the event. One person who was missing from the festivities: Her dad, who RiRi recently said abused her mom while growing up. [P6, NYDN] More

• Rihanna has a new album to promote, which explains why she's suddenly breaking her silence about the personal troubles she's faced over the past year. She addresses the Chris Brown incident in an interview in the current issue of Glamour. And she'll discuss it again on Thursday when she sits down to an interview with Diane Sawyer on Good Morning America. [People, Sun, Glamour]
• Related: Rihanna attended Mariah Carey's Halloween party the other night, but the two divas refused to exchange a word. [P6]
• Kate Hudson says she quit drinking to get ready for a film role (and not because she's pregnant). She also says the diamond ring she's been wearing is not because she's engaged to A-Rod. (She says she isn't.) [P6]More

• Lindsay Lohan may be into boys again, at least according to the Sun, since she supposedly spent the night with a male model who she'd been seen making out with the night before and later posted a picture of her new conquest on Twitter. Whether this is a make-Sam-jealous ploy or true love is hard to say, but rest assured her dad will probably weigh in on the matter by the end of the day. [Sun]
• A brazen jewelry thief busted into Amanda Peet's Tribeca loft on Wednesday and said, "What up, bitch? I live here" to Peet's assistant when she happened to walk in on the guy. He quickly fled, but let's hope she got out a "What up, mo fo?" before he was out of earshot. [P6]
• Jessica Simpson likes "spiritual," "artistic" and "intellectual" men because she "can bore out pretty easily." And now it's totally clear why her relationship with Tony Romo didn't work out. [Extra, People]
• CNN's Lou Dobbs says he's been receiving threatening phone calls and his house was shot at due to his views on immigration. But police don't have any any record that he's reported threats in the past and they think the shot was fired by a hunter. So, per usual, Dobbs is probably just full of crap. [P6]
• Michael Jackson's dad says his son is "worth more dead than when he was alive." The world already knew that was the way he felt, of course. But no one was expecting him to come right out and say it.  [NYP] More

• 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]More

• Madonna is taking a quick trip over to Malawi this weekend "to lay the foundation stone" at the new "multi-million dollar girls school she's building." That's funny. We could swear we heard about another celebrity doing almost exact same thing not too long ago. Oh, yes, her! Hopefully this time around there's a little less controversy. And let's also hope Malawian schoolchildren are ready to study Kabbalah from dawn till dusk. [Reuters]
• In related news, Madonna's ex, Alex Rodriguez, now appears to be taking an interest in Buddhism thanks to girlfriend Kate Hudson. Or at least he's pretending to be interested in it to make her happy. You decide! [NYDN]
• Ashlee Simpson-Wentz—sister of Jessica, wife of Pete, and the character Violet on The CW's Melrose Place—is now unemployed. Melrose's producers are taking a "It's not you, it's me" approach and saying the decision to cut her out of the show had nothing to do with the fact she can't act, but was because that had been their plan for the character from the beginning. [EW, People] More

• Jessica Simpson and Gerard Butler went to Soho House on a date on Tuesday night. Then again, the duo had to be "chaperoned" by friends including Simpson's BFF/hair stylist Ken Paves, which hardly sounds very romantic, does it? [P6]
• It may be over for the most famous lesbian couple in America, Rosie O'Donnell and Kelli Carpenter. Rosie acknowledges the two are having "issues" and says they're trying to work things out. But Carpenter may have already moved out of the home they share in Nyack, which probably isn't a good sign. [People]
• Jill Zarin has no manners. When the "Real Housewife" appeared at the opening of "Memphis" on Broadway the other night, she arrived 30 minutes late and with an entourage in tow and disrupted audience members when they moved into their seats. Then she blabbed for 15 minutes during the show. [P6]More

Spotted | Sienna Miller walking her dog ... Brooke Shields running errands around town ... Lindsay Lohan shopping at Curve on Mercer Street in SoHo and later heading off in an SUV ... Hilary Duff walking to the Gossip Girl set ... Jessica Szohr shopping at The Limited in SoHo ... Matt Damon filming scenes for The Adjustment Bueau in the rain ... Naomi Watts posing for a photo shoot outside the Cooper Square Hotel ... Shia LaBeouf spitting on the sidewalk outside his trailer on the set of Wall Street 2 .. . Michael Urie and America Ferrera shooting scenes for Ugly Betty ... and Jessica Simpson leaving Nobu after having dinner with hair stylist Ken Paves and her mom.

Spotted | Mel Gibson and gal pal Oksana Grigorieva heading into Balthazar for lunch yesterday ... Jessica Simpson leaving the Ritz-Carlton in Midtown ... John Mayer walking around downtown ... Ivanka Trump arriving at a book signing at Barnes & Noble ... Kelly Rutherford heading to the set of Gossip Girl on the Upper West Side while Blake Lively and Chace Crawford talk on a bench nearby ... Matthew Broderick walking son James to school in the West Village ... Celine Dion leaving the Ritz  ... Chris Pine walking by himself ...  and Sarah Jessica Parker making her way to the set of Sex and the City 2 with a bunch of fans following behind her.

J-Date! | Jessica Simpson says she's open to the idea of online dating. [People]

• After another wild day in court, Christie Brinkley and Peter Cook settled their latest round of legal issues yesterday. But not before Brinkley called her ex an "extreme narcissist," and Cook returned the favor by telling reporters she was an "angry, bitter, vindictive woman." At least it's nice to know they still have feelings for each other, though! [NYP, NYDN]
• As easy as it is to picture Courtney Love sitting in front of her computer punching numbers into an Excel spreadsheet, it turns out she may not be the best financial planner in the world. Love owes $300K in back taxes, according to the government. [TMZ]
• Michael Lohan says he knows who Lindsay's drug dealer is and he plans to reveal all in an effort to "save" his daughter. So who is he? "He has no job. He does nothing. All he does is supply everyone in LA." Call us crazy, but supplying "everyone" in LA sounds like a pretty good job to us. [Radar, NYDN]
• Get ready to see a lot more of Megan Fox dressed in, well, not much: Giorgio Armani has tapped her to star in his new underwear ad campaign. [WWD] More

• Heidi Klum and Seal have a new addition to the family: Lou Sulola, who was born on Friday night and joins siblings Johan, Henry, and Leni. [People]
• Tyra Banks ought to be in a good mood today. Not only has she dropped four dress sizes recently, she's been named the "top-earning primetime TV star" by Forbes thanks to the $30 million she's collected over the past year. [Daily Mail, MSNBC]
• The latest legal tiff between Christie Brinkley and Peter Cook is over: The couple has settled their dispute, which means neither of them will be heading off to jail.  [People]
• Was Penelope Cruz sporting a giant sapphire and diamond ring the other night because she really is engaged to Javier Bardem? And did she wear a bulky sweater over her dress because she's pregnant? So many questions, so few answers. Sigh. [P6, NYDN]More

• The gloves are off in the divorce between ex-model Stephanie Seymour and mogul Peter Brant. He claims she blows through $257,000 a month (including $50K a month on clothing alone); has been stealing and/or smashing some of his "pricey art objects"; has a history of abusing drugs; and has been bringing her boyfriend to the house. Team Seymour has yet to respond with its side of the story, but you can be sure it's going to be equally salacious. [P6]
• In other news of warring exes, Christie Brinkley and Peter Cook are back at it. Cook's lawyer says Brinkley violated the couple's divorce settlement and should go to jail because of it. Brinkley's team says it was Cook who is at fault and he should be put in jail. At least they agree on one thing! [NYP]
• Madonna supposedly has real estate brokers hunting for an apartment for Jesus Luz, since she's not ready to have him move in with her. Meanwhile, ex-husband Guy Ritchie has finally gotten around to responding to Madonna's comments that he's "emotionally retarded." In an interview with Esquire, Ritchie responded, "I still love her. But she's retarded, too." [Sun, Esquire]
• Did you know that Dina Lohan has a "celebrity" shoe line called Shoe-Han? She does! And it will be unveiled today at Trump Plaza. Exciting! [P6, People]More

• The Letterman mess rolls on. The Late Show host issued another apology on his show last night, describing how the scandal has impacted his wife, Regina Lasko ("She's been horribly hurt by my behavior"), and kindly pointing out that he's not having sex with any of his current staffers. Meanwhile, Stephanie Birkitt, the woman at the center of the "scandal," supposedly wrote in her diary that she was dating alleged extortionist Robert "Joe" Halderman and sleeping with Letterman as recently as last fall, leading Halderman to flip out when he read her diary in December. [NYP, NYDN]
• So are Penelope Cruz and Javier Bardem engaged? While Cruz's rep went with "no comment," Bardem's flack said, "I really don't know, but would not be able to say anything even if I did." That sounds like a "yes" to us! [People]
• Celebrity chef Todd English skipped out of his wedding at the last minute this past weekend. His jilted bride went ahead with the party anyway, while English headed to South Beach to hit the bars and clubs. Classy. [P6]
• Heidi Klum has filed documents to change her name to "Heidi Samuel," since that's Seal's last name. Please update your address book accordingly. [TMZ]More

• Mischa Barton went to see "Tosca" at the Metropolitan Opera the other night. Naturally, when she showed up and saw a red carpet, she started walking it... until she realized it was for the screening of Michael Moore's new documentary at Alice Tully Hall. It was then that the light bulb went on and she ran across the street. Pull it together, woman! [P6]
• Jessica Simpson can't catch a break. Tony Romo ditched her; her dog got snatched by a coyote; her friends keep dishing to the media; and now her ex, Nick Lachey, appears to be reuniting with his ex, Vanessa Minnillo. Poor Jess. [E!]
• Tyra Banks appeared on Larry King Live last night and talked about how she dealt with packing on some lbs (again), her real hair (again), and how she loves being naked (unless the lighting in the dressing room sucks). [CNN, ET]More