2002: Ryan Phillippe and Reese Witherspoon

Ryan Phillippe and Reese Witherspoon looked like the picture-perfect Hollywood couple. Phillippe, with his mesmerizing eyes, and Witherspoon, with her beauty — not to mention both are great actors who are enjoying their careers. The two first met on Witherspoon’s 21st birthday and were soon spotted dating. After a year, they got married and had their first child. Their son came after a few years later, much to the delight of his parents.

However, their marriage did not last as well because, in 2006, they announced their separation. They went on to have families of their own and remained friends and great co-parents to their children. It seems that they are better off as friends — they both admitted as much. Witherspoon’s career as an actress went full steam, and she accumulated a lot of investment money for her children and her passion projects.