Adapted from screenwriter Stephen Belber's play, this never quite manages to shake off its theatrical origins and stagy style.
Aspiring film-maker Jon (Sean Leonard) arrives in his hometown of Lansing, Michigan to present his latest effort at the local film festival.
Vince (Hawke), a volunteer fireman and small-time drug dealer, is also in town and invites Jon to his motel to discuss the old times.
It's been 10 years since they were a high school together but the under-achieving Vince has always harboured a petty grudge that Jon stole his girlfriend during the senior year. (You've got to let go, Vince.)
They've been over the ground many times before - and it feels like the audience has as well - but Jon finally admits he is not proud of having betrayed his friend.
However, he reasons the romance was short-lived and, from Vince's point of view, patronisingly advises him to let it go and get on with his life.
However, the stubborn Vince persists with his precise line of questioning and eventually elicits a confession from Jon that puts a powder keg under their friendship.
Belber's script contains enough lighter moments for the dialogue between Vince and Jon to never lose its shine although the first hour is essentially a two-hander in the grim motel room.
Things only jump up a gear with the arrival of Amy (Thurman), the girl who caused all the grief but whose cool-headed presence shows up the dodgy motives of both the men.
The script also asks pertinent questions about how people perceive certain situations with the benefit (or handicap) of hindsight and can arrive at totally the wrong conclusions.
The acting - particularly the sleazily quick-witted Hawke - is excellent, although a long way from his last outing in the Oscar-winning Training Day.
While not up there with Linklater's excellent Dazed & Confused, this is an interesting curiosity but never really covers any new ground.
Tim Evans