When: 1989 - July 2010

Sean Penn is infamous for being too elusive to tie down, but for a miraculous moment in time, Robin Wright seemed to be “the one.” Wright, who began dating Penn after his divorce from Madonna in 1989, was in an on-again-off-again relationship with the actor through the early '90s, before marrying him in 1996. After a relatively stable period raising their two children together, rumors of their separation would surface in the 2000s, before they officially announced their divorce in 2009. 

Smash Probability: This relationship exists as the glimmer of hope for any future Sean Penn girlfriend.