But six months later, the reconciliation ended with Wright filing for divorce Aug. 12. According to the legal papers in Marin County, Calif., the estranged couple "agreed to division of all property" and "[shared] custody" of son Hopper Jack, 16. They also have a daughter together, Dylan, 18.
The legal action culminates their roller-coaster relationship, which started when both Wright, 43, and Penn, 49, filed for divorce, citing "irreconcilable differences," on separate occasions in December 2007.
Marital PhasesThe two, who had been together since 1989 and got married in 1993, stopped the divorce proceedings in April 2008. The same day the court clerk dismissed the petition at their request, they were seen together at an Eddie Vedder concert in San Francisco.
"All marriages have their phases," Wright told the U.K. magazine Pscyhologies. "It's life. We go through it, if we're married long enough. If you're lucky you grow and you work it out."
Though they tried to patch things up, Penn again filed for legal separation from Wright in April 2009 – only to rescind his decision a month later.
Stepping Out with Other WomenDuring their time apart, Penn stepped out with two famous faces. In February 2008, the actor hit an Oscar after party in L.A. with model Petra Nemcova, though neither addressed their relationship.
But when tabloids reports linked the Oscar-winner with Natalie Portman in May 2009, Portman made it clear they weren't an item. "Sean Penn is a friend and colleague," she said at the time. "The reports that we are romantically involved are completely untrue."
As for Wright, the actress remained low-key and tight-lipped throughout their 2-year separation.
"She was very non-talktative about Sean ... never, never, never would she talk about him," a producer who worked with Wright in 2008 tells PEOPLE. "She was unhappy [during the divorce rumors] and showed a lot of vulnerability."
But a year and a half later, Wright says she's passed that point and is content with life as is.
"I know what I don't want," she tells More magazine's September issue. Still, "I have no regrets. I, we, have two amazing children we raised together.'"
Reporting by KEN LEE and NATASHA STOYNOFF