ANNA KOURNIKOVA AND ENRIQUE IGLESIAS – 19 YEARS

Until today, Anna Kournikova and Enrique Iglesias remain mum about their romance. The two first met on the set of the music video of Iglesias’ song, Escape, in 2001. Since then, they reportedly started a romance that nobody knew about. Anna Kournikova is a Russian former professional tennis player and American TELEVISION personality. Her looks and celebrity status have made her one of the most famous tennis stars in the world. Despite never winning a singles title, she reached no. 8 in the world in 2000. She had more success in doubles, sometimes even the world no. 1.

They seemed to make things official when they walked the red carpet together in 2002. In 2004, Kournikova was seen wearing a pink diamond earring that gave birth to engagement rumors. However, they never confirmed or denied it. In 2007, Iglesias revealed that they already got married, but hired divorce lawyers as they were allegedly already separated. Fast forward to today, they are still together and already had three kids.