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Russian tennis star Anna Kournikova, whose good looks have long eclipsed her court skills first wowed crowds as a teenager in the late 1990s and became known as the "Britney Spears of Tennis" although she never won a major tournament before announcing her retirement from professional tennis in March 2004. Kournikova and  Latin crooner, Enrique Iglesius, have been dating since she appeared playing his girlfriend in the 2002 music video for his hit "Escape".  
 
 
 
Anna's Engagement Ring
Enrique sealed the deal with Anna with a monstrous 11 carat natural pink pear shape diamond in a simple semi-mount with diamond accents. The ring comes from the world's biggest mine in Argyle in western Australia, where diamonds have a unique champagne and cognac color. Estimated Value: $5.4 million.

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