A Timeline of Enrique Iglesias and Anna Kournikova's 16-Year Romance

At her World Team Tennis match in 2004, Anna wore a gigantic pink diamond ring on that finger and immediately sparked engagement rumors. The two never confirmed anything, but Anna did keep wearing it until she switched to a simple silver wedding band later that year.

In 2006, Enrique and Anna seemed to get more comfortable with flaunting their love for the world to see. They were spotted at different sporting events like the NBA finals game between the Dallas Mavericks and the Miami Heat as well as hitting up restaurants in Miami. After 2006, the two went back to keeping an extremely low profile. They were rarely seen out in public together and didn't discuss their romance with the press.