39.Ryan Reynolds and Alanis Morissette

For those who do not know, Ryan Reynolds and Alanis Morissette were once engaged to be married. As years went by and Reynolds got big, he is now known for his box-office hits and well associated with his marriage and family life with Blake Lively.
In 2002, Reynolds and Morissette started dating. They give credit Drew Barrymore for inviting them to her party that year which led to their relationship. Morissette was already a music personality since 1995 for her hit album Jagged Little Pill, while Reynolds had just gotten his big break when he landed the Van Wilder role in 2002.

The couple was often part of Hollywood news scoop as they attended events together. At some point, they even got engaged in 2004. Sadly, they called it off and broke up after three years of being engaged and five years of dating. They chose not to divulge the reason for their separation in respect for each other, but the You Oughta Know singer hinted that their high profile is the cause. Reynolds later met Lively on the set of Green Lantern in 2011 and married her in 2014. Morissette found the kind of love she wanted with the rapper Souleye, with whom she shares three children.