These two have been dating since 2002 and were even rumored to be married. They've never confirmed the buzz, but it's highly speculated that they are indeed hitched. Still, it's not true until they say it's true, right?
Otherwise, Iglesias has been in a few other high-profile relationships over the years. He dated Playboy model Samantha Torres in the '90s, had a fling with Christina Aguilera (allegedly) in 1998, was rumored to be with Jennifer Love Hewitt in 2001, and then got with the tennis star and has been with her since. However, there were some scandalous rumors that the singer hooked up with an Irish actress in a bathroom in England in 2004, though, of course, that's wildly speculated.
Enrique Iglesias dated Samantha Torres
Enrique Iglesias and Playboy model Samantha Torres dated back in 1997.
Enrique Iglesias had a fling with Christina Aguilera
Enrique Iglesias was rumored to be with Jennifer Love Hewitt
Jennifer Love Hewitt and Enrique Iglesias were rumored to have had a fling in 2001 when she worked with him on the video for 'Hero.'
Enrique Iglesias was rumored to be with Emma Kearney
2002 - Present
Enrique Iglesias is dating Anna Kournikova
In late 2001, Kournikova starred in Enrique's "Escape" video. In 2003 and again in 2005, rumors of their secret wedding spread but the two did not confirm or deny the marriage. In a 2010 interview, Kournikova confirmed that she and Iglesias have been together for over eight years but have no plans to marry in the near future.