• If the daughter of fashion's most powerful figure can't find a job, how are those of us with less cushy connections expected to? Anna Wintour says daughter Bee Shaffer has gone on 24 job interviews since graduating from Columbia last spring, but has yet to receive a single offer. [NYDN]
• Is Tinsley Mortimer finally getting the reality show she's been dreaming about? Let's hope so! [P6]
• The good news: Jennifer Aniston and Gerard Butler had a rendezvous in LA the other night and were acting all lovey-dovey. The bad: Then they got in their cars and drove in totally different directions. [P6]
• Some customer tried to tip the Olsen twins during Fashion's Night Out at Bergdorf last night after they served him a drink. Did the girls keep the money? Give it back? We're going to assume the former for the time being. [NYDN]

Fashion's Night Out went down last night. Did you take part in the "largest single shopping event in the city's history" and actually do some shopping? Or did you just marvel at the spectacle of it all: Anna Wintour, Michael Kors, Diane von Furstenberg, and Kate Hudson stepping foot inside a Macy's in Queens; Justin Timberlake greeting fans at Saks; Charlize Theron putting in an appearance at Dior; Oscar de la Renta belting out a few tunes with Sarah Jessica Parker, Barbara Walters and Bette Midler; the Olsen twins bartending at Bergdorf, not far from where Posh Spice was signing t-shirts and Padma Lakshmi was judging a cook-off. (And on and on and on.)

Fashion's Night Out, Anna Wintour's faux charity event to make people shop, is well underway. What's Anna up to? We followed her to the Macy's in Queens to find out. Too bad we were the only ones there for her.

So, while Hamilton was asking Julia Allison about her freelance rate for the item below she hopped on IM to ask what he was writing. Also she wanted to lodge a reader complaint about the direction of recent Gawker coverage.

[Sometimes nude model, former gossip columnist, and full-time heiress Lydia Hearst at the Haleh fashion show. Image by WireImage via Getty]

Demi Moore won't respond to the British Prime Minister's wife. Victoria Beckham won't respond to questions about her tits. And Hugh Hefner doesn't respond well to his wife's infidelity. Oh, yes, it's your Thursday morning Gossip Roundup!

After reading her Anna Wintour's review of London nightclubs, we wanted to know more about her Gossip Girl younger years as a club-hopping high school hipster. Thanks to Jerry Oppenheimer's book Front Row we compiled this index

McKinsey consultants are very close to completing their evaluation of Conde Nast and all of its glorious over-consumption. This can only mean one thing: the dismantling of a publishing empire and, also, countless unborn dreams.

Did Anna Wintour ever strike you as the type who was a precocious teenager, hanging out in the "discotheques" of mod 1960s London? Suspicions confirmed! We have a copy of a nightlife review a 17-year-old Wintour wrote in 1966.

Intrepid reporter John Koblin of the New York Observer caught Anna Wintour at the U.S. Open watching her crush Roger Federer's match against Lleyton Hewitt. He asked Wintour the two don't-ask-don't-tell talking points on everyone's mind: McKinsey and Federer. Results?

[Anna Wintour exercises some rarely used muscles while attending a match between Simon Gruel and her make-believe boyfriend Roger Federer at the U.S. Open last night. Image via Getty]

New court papers have Wolfgang Puck's wife dissing everyone from Anna Wintour to Shaquille O'Neal and proclaiming herself "the new Bill Gates." It's the inevitable trainwreck ending to a food huckster's partnership with a group of internet speculators.

The September Issue debuted in New York over the weekend. So how did it do? Very well, actually: The film grossed a total of $240,078 on six screens, making it the fifth-best documentary debut ever. And you can't say Anna Wintour didn't do her part to support the film: At least ten of those dollars came out of her own pocket.

Anna Wintour apparently couldn't get enough of The September Issue, for she was snapped waiting in line to see the fashionable documentary this weekend. How pedestrian! The girl behind Wintour obviously recognizes the Vogue editrix and looks appropriately fearful.

We already told you how the Vogue creative director stole the movie from Anna, but now it appears the editor-in-chief is not only letting her have the win, but promoting her as well...with Vogue!...on the internet!

• The Carolina Herrera dress that Anna Wintour wore on Dave Letterman's show this week? She wore it to the CFDA Awards back in June. Uh oh! [Stylelist]
• Zac Posen is the latest designer to bid goodbye to Bryant Park this Fashion Week. He'll be staging his show at The Altman Building instead. [WWD]
• Another good thing about the recession: There are fewer crappy catalogs getting stuffed in your mailbox. [AP]
• The September Issue doesn't open in theaters until Friday, but it seems some people (above) are already sick of all the publicity. [NYShitty]

Anna Wintour's Make-People-Like-Me-Before-My-Contract-Is-Up Tour 2009 needed a charitable arm. She came up with Fashion's Night Out, a plan to save the industry, the economy, and her job all at once. But it's not a charity, it's a power play.

Because the fashion industry really, really wants you start shopping again, it's pulling out all the stops for Fashion's Night Out, the hyped-up retail pep rally scheduled for September 10. The latest PR offensive: A TV commercial featuring Sarah Jessica Parker, Anna Wintour, Diane von Furstenberg, Donna Karan, Oscar de la Renta, Carolina Herrera, Isaac Mizrahi, Diddy, Tory Burch, Lazaro Hernandez, Ashley Olsen, and a whole bunch of others—all jam-packed into a spot that's less than a minute long. If you watch the commercial—and you can do so above—make sure you're paying attention at the 0:30 mark. It's not every day that you get to see Anna Wintour come off as a giddy schoolgirl.

• Lindsay Lohan says she feels "scared" and "violated" after the break-in at her LA home last weekend. (We're guessing that's the same way Sam Ronson feels when she comes home to find LiLo waiting for her in the bushes, but what do we know?) In related news, though, Lohan's neighbors are now hoping she'll pick a new neighborhood to terrorize. [Sun, NYDN]
• Things don't always go Anna Wintour's way. When she headed to dinner after her David Letterman taping the other night, the poor editrix had to wait 20 minutes for her boyfriend, Shelby Bryan, to show up. And then the restaurant had the nerve to try and seat them at a non-private table. The indignity! [P6]
• Chelsea Handler has dumped her boyfriend, Ted Harbert. Making matters a little awkward: Harbert runs E!, which means her ex is still her boss. [NYDN]
• Cindy Crawford is coming clean about a deep, dark secret. She says that although you might have thought she had a perfect body, she really does have a bit of cellulite. Guess you'll have to focus on her inner beauty instead. [Star]

Anna Wintour wants to stay out of the limelight, Lily Allen's friends talk trash, and Mel Gibson's girlfriend's unborn child is totally making her fat. All that and more in your Wednesday morning Gossip Roundup!