The Judges

Rachel Greenwald
Matchmaker and author of Find a Husband After 35 (Using What I learned at Harvard Business School)

Pamela Paul
Relationship expert and author of The Starter Marriage.

Anonymous Odds Maker
From popular betting site bodog.com

The Odds

Kid Rock and Pamela Anderson (Odds 20/1)
RG: Any couple that has wedding celebrations in Beverly Hills, Detroit, and Nashville, is focused on making a statement in the public realm, not creating a lasting, private bond between two people. They won't last.
PP: They have a very small chance of success. Stepchildren are involved and they've already gone through public breakups.

Chris Martin and Gwyneth Paltrow (Odds 1/1)
RG: She met him shortly after her father died. It was a terribly emotional time in her life, and she probably saw things in him that reminded her of her dad's best qualities. Sharing a time of tragedy bonds two people forever. They'll make it.
PP: Their chances of making it are medium to high. They married at an appropriate age and having two kids together tends to bond a couple.

Nicole Kidman and Keith Urban (7/3)
RG: She waited five years to remarry after her divorce—and not rushing into the arms of another after heartbreak bodes well for the future. They also have similar backgrounds, which helps them understand each other's values and professional pressures. They'll make it last.
PP: They've got middling to poor chances of making it. She has a previous marriage, he's a recovering addict, and there are stepchildren involved. On the plus side, they did get married at an older age.

Guy Ritchie and Madonna (4/1)
RG: She is the master of reinvention, which is a great skill for success in marriage. There are many phases and shifts in marriage, and one needs to adapt, to evolve. Despite her public image as "the wild child," they'll make it.
PP: They have middle to low chances of making it. There is an age difference, she was previously married, they've got cross-cultural differences, and there is a stepchild involved

Ashton Kutcher and Demi Moore (13/7)
RG: It's hard to find great men in the same peer group who are looking for a wife over 40. Their union proves that love can come in unexpected packages if you're open-minded. They'll make it.
PP: Though she was married with kids, her marriage was relatively long and stable. They have middling chances of making it

Cameron Diaz and Justin Timberlake (4/1)
RG: Any couple who can claim victory for "The Best Burp Award" (Nickelodeon Kid's Choice Awards; she won in 2002, he won in 2003) has a great sense of humor. Despite the age difference, they have fun together, and it's important to go through life with a partner who makes you laugh and feel goofy. They'll make it.
PP: They have middle to low chances of making it. They've got a significant age difference and will always be in the shadow of the "Britney Factor."