I guess the second time around wasn’t enough to heal the differences. Actor Sean Penn has filed for legal separation from actress-wife Robin Wright Penn last Friday. Back in 2007, Robin first filed for divorce before the couple decided to give their marriage another try, but it appears that reconciliation was not a success. No reason was given why the two might be ending their almost 13 year marriage, but one has to wonder if it has anything to do with Seans’ “playboy” lifestyle.

Recently, “Hollywood Dame” had reported about a slew of rumors going around about Mr. Penn’s affair with fellow actress Natalie Portman before the 2009 Academy Awards. Could Portman possibly be a homewrecker in this relationships demise? (To Read About Their Alleged Affair Click HERE.)

Sean is coming off of a huge career boost, having won the Best Actor Oscar for his role as gay politician Harvey Milk in “Milk“. The couple has been since 1996 and have two teenage children together, Dylan and Hopper Jack. Last time they separated the couple asked for joint custody of their children, although there’s no word as to what this filing is requesting.

Think they’ll change their mind again?

Images Via: Wenn, Getty