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."
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Beyoncé Knowles and Jay-z (7/3)
RG: Keeping their relationship private is a sign that it's actually important to them. Her parents have been married 24 years, which is another good sign: she knows what it takes to see a relationship through good times and bad. Despite her youth and his bad-boy public image, they'll make it.
PP: They have a significant age difference, and she has not yet reached the average age of first marriage. The younger people are when they first get married, the more likely they are to end up in divorce. But these two have been dating for quite a while. You never know—they might make it.
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Brad Pitt and Angelina Jolie (19/4)
RG: In all my years as a dating coach and matchmaker, I've never once seen the "other woman" end up happy in the relationship she's stolen. They won't last.
PP: They have middling chances of making it. She was married twice, he was also married, and they have high-powered careers that require extensive travel. On the plus side it seems like they are serious about a life-long commitment because they have adopted kids and a birth child.