Two weeks ago the news surfaced that Viacom chief Sumner Redstone and his second wife, Paula Fortunato, were divorcing after five years of marriage. Much was made of Redstone and Fortunato's 39-year age gap and the couple's pre-nup, which will provide Fortunato with a $5 million fortuno for the five years she spent by the not-so-healthy billionaire's side. But she's hardly the only one who has been married to someone who could easily pass for her father or granddad. After the jump, a list of famous New York couples and their equally famous age gaps.

♦ Madonna and Alex Rodriguez were able to fly out to the Hamptons for a "quick and cozy rendezvous" without anyone knowing, but only because Jerry and Jessica Seinfeld picked the couple up (separately) from the East Hampton airport and let them hang out for several hours at their waterfront manse. [P6, The Sun]
♦ With her husband Rossano Rubicondi filming a reality show in Italy, Ivana Trump has been hanging out with a 23-year-old Belgian model named Marius Rusovici. [P6]
♦ Tina Brown and Cathie Black are enemies, apparently, since they "disagreed on just about everything" and "wouldn't even look at each other," at a conference this week. [R&M]
♦ Is John McCain making an Saturday Night Live appearance this weekend? Does anyone care? [MSNBC]

When it comes to Sarah Palin, you've probably heard every rumor and allegation over the past last month. But here's one more piece of Palin news to make your jaw drop: Eight years ago, Sarah Palin drove two hours to Anchorage to attend an Ivana Trump event where she stood in line to purchase a bottle of Ivana's perfume and an autographed copy of her book. Disturbing, isn't it? Naturally, Ivana is solidly behind her former fan/small-town mayor-turned-vice presidential candidate: "We have a lot in common. She's down to earth; I'm down to earth. In business, I use the skills I picked up as a ski champion rather than shooting moose, but there's nothing wrong with that." [P6 Mag]

♦ Not only did Jennifer Lopez and Marc Anthony renew their vows at 3:15 a.m. in Las Vegas on Sunday, they did it in a joint ceremony with Mets outfielder Carlos Beltran and his wife Jessica. [E!, People]
♦ Lindsay Lohan and Samantha Ronson tell friends they're planning on dressing up as Todd and Sarah Palin for Halloween. [NYDN]
♦ Jay-Z couldn't get any London clubs to pay his $50,000 appearance fee this weekend. [This London Blog via E!]
♦ Is Suri Cruise lonely and sad because has no friends her own age? [P6]

The price of marrying someone much younger and prettier than yourself is that they might not be the sharpest knife in the drawer. Uber-cougar Ivana Trump can laugh about it, though, as she did when her fourth and current husband, thirty-something Italian Rossano Rubicondi, put his lifejacket on the wrong way during an emergency drill aboard a Mediterranean cruise. "If something happens, you're floating facedown," she admonished him. Given Ivana's propensity for falling down on yachts, someone needs to keep their wits about them! [Page Six Magazine]

♦ Scarlett Johansson is a married woman: She tied the knot with actor Ryan Reynolds in a small ceremony outside of Vancouver on Saturday. [Us]
♦ Heather Locklear was arrested for driving under the influence of prescription drugs in Montecito, CA, on Saturday. [NYP]
♦ Heath Ledger's daughter Matilda will inherit his entire estate, which is estimated to be worth $20 million. [NYP]

♦ It seems like sending out company-wide emails ripping your co-workers is not a good idea: Pat O'Brien has been fired from The Insider. [R&M, P6]
♦ Brandon Davis has been conning his friends out of cash, but whenever anyone tries to get the money back "he starts crying and gets them to feel bad for him." [P6]
♦ Poor Ivana Trump almost had to fly coach this week. But then someone in first class switched seats, so everything turned out okay. Phew. [P6]
♦ Heather Mills is suing her former publicist—the one who very publicly dumped her and called her a "witch"—for libel. [P6]
♦ Anne Hathaway's been crashing on her parents' couch ever since she got booted from Raffaello Follieri's duplex. [In Touch]

♦ At Marc Jacobs, there were lots of celebs like Helena Christensen, Elijah Wood, Nicole Richie, Stephanie Seymour, Kelly Osbourne, Sofia Coppola, Winona Ryder, and Jennifer Lopez, and the elaborate, adventurous, world travel-inspired clothes got high marks—but all of the above was entirely eclipsed by the presence of Posh Spice's new gamine haircut. [WWD, Telegraph, Hello]

Page Six Magazine's Sixoholic column regularly provides various socialite-heiresses the chance to embarrass themselves in print. We love it—and we'd also love to see what said columns look like before being edited for grammar and spelling. From Lydia Hearst to Ivana Trump, they never let us down with their musings: this week, the 59-year-old Trump (recently married to a dubious 36-year-old Italian), tells us that she's not above tying her one-year-old granddaughter to a leash:"I'll probably put her on a leash [to teach her to ski], like a dog. It is a technique. You maintain control from the back so she cannot just take off through the woods." That is actually adorable. But seriously, what's with her man, Rossano Rubicondi?

1) The final big event of the season was the Robert Wilson-hosted concert benefit at the Watermill Center on Saturday. Rufus Wainwright, Kate, Anna and Martha McGarrigle, and Jessye Norman performed for a crowd including Isabella Rossellini, Calvin Klein, Amanda Hearst, Steven Klein, Daphne Guinness, Patrick McMullan, Bob Colacello, Jamee Gregory, Beth Rudin DeWoody, Luigi Tadini, and Lisa Anastos. [Paper/PMc]

Last week, Quest magazine, coddler of heiresses, financiers, and other layabouts, published its annual "Quest 400," the exhaustive yet unexplained list of the society fixtures it deems worthy. Originally the "400" represented the number of guests Mrs. Astor could fit into her ballroom. Mrs. Astor is long gone, so how can one land a spot on the list today? We looked through all 20 pages to find out how to make the cut.

Pamela Anderson walking from the St. Regis to Central Park with her son ... Tori Spelling and a friend looking lost in Midtown ... Naomi Watts taking a walk downtown with her son ... Mariska Hargitay and Luke Perry shooting scenes for Law & Order: SVU in Inwood ... Ivana Trump strolling down Madison ... Katie Holmes leaving an office building wearing baggy men's jeans ... Maria Bello posing outside NBC studios ... Antonio Sabato Jr. outside the CW11 studio ... Rebecca Romijn shooting a scene on the set of Ugly Betty ... Sarah Jessica Parker and Matthew Broderick leaving a restaurant in Midtown ... and Rihanna leaving Da Silvano with a group of friends.

• Alex Rodriguez is expected to file divorce papers of his own in a Miami court today: He's wants his prenup enforced and any charges that he cheated on wife Cynthia removed from the record. [NYDN]

• Ashley Dupre's reps, who have been negotiating deals on her behalf, say she's interested in "journalism and lounge singing," and that she "sees herself as a kind of Dr. Phil." Appropriately, the $2 million TV offer she's considering would team her up with the producer to reunited Joey Buttafuoco and Amy Fisher. [NYP]

• Ivanka Trump and Jared Kushner may be back together, possibly because Ivanka has agreed to convert to Judaism if the relationship gets serious. [Page Six]

There's one group of political donors that rarely receives any credit for their generosity. They don't get invited to any gala dinners or fancy cocktail parties, nor can they expect their checks to earn them any consideration when the next president is thinking about, say, who to appoint the Ambassador to Jamaica. They're the sons and daughters of the ridiculously wealthy, who kindly lend their names/identities to mom and dad so their hyper-political parents can direct even more cash to their favorite candidate. Of course, there's nothing illegal about any of this. Nor is it totally impossible that a 19-year-old college student would decide she'd rather give $4,700 to Hillary Clinton rather than, say, stock up on Juicy tracksuits. (Or Jared Kushner making his first big donation to the Democratic party when he was just 11.) Below, 2008 presidential donations by the children of some of New York's richest and powerful.

• Naomi Campbell pleaded guilty today to all six counts in connection with her assault on a police officer at Heathrow back in April. A sentencing date hasn't been set, but she's looking at a maximum six-month prison sentence and a $10,000 fine. We bet garbage duty in New York's looking a whole lot better now. [Daily Telegraph]

• Former New Jersey Gov. Jim McGreevey had a messy day in court yesterday. He's in debt to the tune of hundreds of thousands of dollars thanks to legal fees and alimony payments. Plus, he's got to pay his partner, Mark O'Donnell (who works for billionaire developer Charles Kushner) $3,000 a month in rent. True love! [NJ.com]

[Famous divorcée Ivana Trump on vacation in St. Barth's yesterday; image via Bauer-Griffin]

Ivana is the ex-wife of Donald Trump and the mother of three of his five kids-Ivanka, Don Jr., and Eric.