Shakira And Antonio de la Rua
Length of Engagement: 10 years

The two were engaged for a decade before going their separate ways in 2011. De la Rua is an investment banker and the son of the former president of Argentina, Fernando de la Rua. The two ultimately decided that they weren't right for each other in the end. 

“Our friendship is solid like a rock. It will always be this way and I will always be by his side, but as a working companion and as a friend. Antonio is the person in whom I most confide in this world. Together with him I was able to get to where I am today," Shakira shared with Argentine celebrity magazine Luz.