Anna Kournikova and Enrique Iglesias

Anna Kournikova and Enrique Iglesias were struck by Cupid’s arrow, and their love story has since blossomed into one of Hollywood’s most robust and secretive relationships. The Latin Pop King and the former tennis ace first locked eyes on the set of Iglesias’ “Escape” music video in December 2001, where they shared a passionate kiss in a car.

Despite publicly announcing their romance in August 2002, the couple has opted to keep most aspects of their personal lives under wraps while raising their three children together. Marriage might not be on the cards for them, but their two-decade-long bond remains an enigma to many.