Ryan Phillippe and Reese Witherspoon

Reese Witherspoon’s 21st birthday party was the reason she met Ryan Phillippe. In 1997, he was present at the event, and Reese, who spotted him, approached him and said that he must have been a gift sent to her that day. Since then, the two dated and slowly rose to become one of the most popular celebrity couples in Hollywood. Within only a year of dating, they got engaged and got pregnant with their first child.

They tied the knot in 1999. Reese walked down the aisle six months pregnant. They had Ava, their firstborn shortly after that. Within four years, they had Deacon, their second kid soon after. The couple was celebrated as their family and their investments were growing. In 2006, however, they decided to part ways. Ryan said in an interview that the marriage probably didn’t work because they were both so young and things happened very fast.