I think Gregory Smith is probably a good actor. He comes from doing Television (Everwood) and is probably looking for something off the beaten path to make people notice him but to do that he'll need something with range and he couldn't have gotten any more vapid and empty than the character he plays, Henry Nearing. He has no characteristics, no depth, no good dialog and I don't blame that on Smith other than he should have read the script better. Ashley Johnson is decent enough, and probably has more depth than most of the other characters combined as the next door neighbor best friend of Henry. Johnson is at least still baby faced enough to pull off the High School look but her and Smith have zero chemistry as soul mates and best friends. David Morse is a hell of an actor. He has had some amazing roles and done some terrific work and somehow they shoved him into this emotionless dull portrait of a grieving man (having lost his wife) turned to alcohol and looks like a hippie. They should have left the story and character building to his character because if anyone in this cast could have pulled it off it would have been Morse but he falls flat with this script. And finally we come to the lovely Jordana Brewster. The girl is sexy, there is no doubt about it, but that doesn't even come close to carrying a film. Her wild and crazy portrayal of the object of Henry's affections, Grace Chance, is not even close to what it should be. She looks so much older than she should be (which she is,) they give no explanation as to her characters flaws or reasoning, only that she appears to be a skank who wants to seduce Henry for no particular reason. Brewster and Smith actually do have decent chemistry and there are some steamy love scenes and a cute little "our clothes are gone let's run through the streets" scene but you just don't give a lick about their characters or what happens to them and you feel yourself begging to know more.
So many characters, so much potential to explain them all and yet never happens. You never get to care or find out any information but rather just watch Henry have this steamy little fling and then somehow learn from it and graduate. It's a bore-fest plain and simple. I don't know who to blame but I think it's mostly to rest on the shoulders of the writers and the director because they tried to create something that at best might be an "R" rated episode of Dawson's Creek but even that was far more entertaining than Nearing Grace could ever be (witty title by the way.) Steer clear of this indie film because it has Brad Renfro and Dominique Swain written all over it and if you know what I mean by that you'll know how bad this really is. 3/10