Answer for 9.02.2008's UMQotD!

Chasing Amy(IMDb)(IHM)(Rotten) is correct... Now don't go thinking this is a Kevin Smith week or anything because its not... Everything is going well for our two comic book writers, until they meet another comic book writer who is a lesbian, and one of them fall for her... Then all hell breaks loose. Finger Cuffs, Every mans dream and the not so happy ending... Directed by Kevin Smith(IMDb) and starring Ethan Suplee(IMDb), Ben Affleck(IMDb), Jason Lee(IMDb), Casey Affleck(IMDb), Dwight Ewell(IMDb), Brian O'Halloran(IMDb), Jason Mewes(IMDb) and Matt Damon(IMDb). And your eyecandy Joey Lauren Adams(IMDb), Guinevere Turner(IMDb) and Carmen Llywelyn(IMDb).