Don's Plum (2001)

Tonight, like every Saturday night, the guys, Brad (Scott Bloom), Jeremy (Kevin Connolly), Ian (Tobey Maguire), and Derek (Leonado DiCaprio) will hook up together at their favorite chill spot, Don's Plum. And tonight's big challenge, as usual, is to bring a chick. For BRAD, this is easy. He already got with the girl of his choice, SARA (Jenny Lewis), earlier that evening, and she's agreed to come along and meet his friends. JEREMY, takes the adventorous and more dangerous route and brings along AMY (Amber Benson), a girl that he picks up hitching in the streets of Los Angeles. IAN, doesn't have it so good, at first, as one chick after the next refuses his invitation, but hten along comes JULIET (Meadow Sisto), who surprises him by agreeing to come along and hang out with his friends. And, Derek, well, he's just not having any luck. No matter how many girls he gets on the line, it looks like he's just not getting any love tonight. So what happens when four guys, and three girls gather at a café and meet a fourth unexpected girl? What goes down when the all cram into a booth in the middle of the night at a local diner? Just about anything!