Enrique Iglesias & Anna Kournikova

Enrique Iglesias and Anna Kournikova have been in love for two decades now and have always lived by their own rules. At least two breakups, a determination to postpone marriage entirely, massive career investments, and not one but two top-secret pregnancies are all part of their love story.

Iglesias claimed that dating Kournikova was “the only meaningful relationship he ever had.” He appears to be content to keep it that way. They are now focused on raising their three young children, and they couldn’t be happier. The couple first met on his Escape music video shooting back in 2001, and began dating soon after. Simply watching the video will reveal the couple’s undeniable chemistry. If there’s one thing they have proven over the years, they don’t believe in marriage – and that’s fine. Fortunately, when it comes to marriage, they’re on the same page, which has resulted in a successful partnership.