‘The Parent Trap’ actress, who had been recently spotted nuzzling the veteran at his private dinner organized for gay activist Harvey Milk, is reportedly looking to perk up her career by starring along side Penn.

The singer, whose many films such as ‘Georgia Rule’ have crashed at the box office, had been heard discussing the possibility with director Gus Van Sant.

“Lindsay and Sean were talking about possibly doing a film together. Lindsay seems like she was really into the idea,” Contactmusic quoted a source as telling Page Six.

Lindsay’s third album ‘Spirit In The Dark’ is set to hit the shelves in 2009 while her love life with girlfriend Samantha Ronson has been at the centre of celebrity and tabloid journalism.