Dinner and a Movie (2001)

Katie is a serious documentary filmmaker. She's frustrated because she's about to hit 32, yet still can't find any highbrow work that would get her career going. For instance, her dream project is to make a documentary about the famous 20th century Russian writer and dissident Aleksandr Solzhenitsyn. Since no one wants to finance such project, she agrees to be a director for hire for TV producer Arlene, who gives her an assignment she couldn't hate more. She is to shoot a documentary series about the life of singles dating in a big city. Her friend and cameraman Spider, who has a crush on her, joins her. Their subject turns out to be Jed, a handsome self-centered guy completely oblivious to the proper dating etiquette. Every date he goes to, he inadvertently turns into a disaster, which makes for great television. Katie grows to like Jed and decides to try to help him become a better dater.