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John F. Kennedy and Marilyn Monroe. Tom Hayden and Jane Fonda. Prince Rainier of Monaco and Grace Kelly. Ever since there have been stars, politicians, royals and world leaders have been bedding them, wedding them and disposing of them. Now, with French President Nicolas Sarkozy and Carla Bruni rumored to be tying the knot, the world may get its first supermodel-cum-first lady. And why not? She’s beautiful. She’s smart. She’s certainly good at getting what she wants. And just imagine the extra press she’ll generate for Chanel, Dior, et al.? With that in mind, WWD decided to play “The Dating Game.” Here, a list of some suggested pairings:

1. Bill Clinton, former president of the United States, age 61; Gisele Bündchen, age 27
Pro: Clinton can’t resist a bodacious babe.
Con: Given his choices of extramarital picks, would he even appreciate the buxom Brazilian supermodel? And could he outpass the Patriots’ Tom Brady?

This story first appeared in the January 22, 2008 issue of WWD. Subscribe Today.

2. Hillary Clinton, presidential candidate and U.S. Senator, 60; David Gandy, 28
Pro: At this point, she certainly deserves it.
Con: Her inherent contradiction is that she’s both a feminist and a masochist. Whether Bill is messing around or messing up her campaign, she stands by him.

3. Barack Obama, presidential candidate and U.S. Senator, 46; Daria Werbowy, 24
Pro: The Canadian Werbowy can educate Obama about the intricacies of universal health care.
Con: His real-life wife is about as beautiful and actually has a job that involves using her fine brain.

4. George W. Bush, President of the United States, 61; Christy Turlington, 39
Pro: She could school him on her pet causes (the environment, Darfur) and make him feel Zen about retirement by teaching him yoga.
Con: Would Bush really downward dog? Would he really listen to anyone — even a beautiful woman — who tells him global warming is a reality?

5. Crown Prince Abdullah of Saudi Arabia, 83; Yasmeen Ghauri, 36
Pro: Despite what her scantily clad Victoria’s Secret spreads may suggest, the Nineties supermodel is of Muslim descent.
Con: Ghauri, whose father is the former imam of the Quebec Islamic community, was once inspired to become more religiously devout after visiting Saudi Arabia. “I thought, OK, OK…I’m going to cover my head and everything. Then I woke up and said, ‘This is ridiculous.'”

6. Mahmoud Ahmadinejad, President of Iran, 51; Janice Dickinson, age unknown
Pro: Both kooky and both blind to how they come off to the rest of the world. And with past lovers like Grace Jones and Kelly LeBrock (in addition to Sylvester Stallone and Dolph Lundgren), Dickinson could educate him about homosexuality, which he says doesn’t exist in his country.
Con: Don’t speak the same language; it’s hard to imagine her taking orders.

7. Hassanal Bolkiah, Sultan of Brunei, 61; Elle Macpherson, 43
Pro: The Sultan certainly appreciates the female form: The royal family owns boats named Tits, Nipple 1 and Nipple 2. And The Body has the requisite curves.
Con: He’d have to get more boats to name after all of Elle’s parts.

8. Giorgio Napolitano, President of Italy, 82; Sophie Dahl, 30
Pro: He reportedly writes poetry. So does she. He acted in his youth. So did she. And there’s great shopping in Italy.
Con: He’s a little old.

9. Tony Blair, former prime minister of the U.K., 54; Kate Moss, 34
Pro: He’s desperate to get back into the limelight; the limelight finds Moss anywhere.
Con: Moss isn’t exactly the poster child for the war
on drugs.

10. Cristina Fernández de Kirchner, President of Argentina, 54; Markus Schenkenberg, 39.
Pro: He doesn’t see being a sex object as feminizing, and she doesn’t feel 6-inch pumps undercut her authority.
Con: Her husband.

11. Vladimir Putin, President of the Russian Federation, 55; Natalia Vodianova, 25
Pro: She’s practically the poster girl for New Russia.
Con: No model can stay that thin with all those
state dinners.

12. Angela Merkel, Chancellor of Germany, 53; Tyson Beckford, 37
Pro: They both have had their fair share of accolades. Forbes declared Merkel “the most powerful woman in the world.” He’s been a VH1 Man of the Year, and made it onto People’s “50 Most Beautiful People” list in 1995.
Con: Hosting “Make Me a Supermodel” keeps Beckford Stateside; chancellor duties keep Merkel in Deutschland.

13. Toomas Ilves, President of Estonia, age 54; Carmen Kass, age 29
Pro: Both active in Estonian politics (Kass campaigned to be a member of the European Parliament in 2004 when Estonia joined the European Union).
Con: He’s a laid-back Libra and she’s a detail-oriented Virgo — they are astrologically incompatible.

14. Mitt Romney, Republican presidential candidate, 60. Naomi Campbell, 37
Pro: He’s the kind of man she likes — rich. And she’d be a powerful new face for the Mormon Church.
Con: She prefers Communists. Just ask Fidel Castro and Hugo Chavez. But since Romney seems to change his position every five minutes, there’s still hope.

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