Gray (Heather Graham) and Sam (Tom Cavanagh) are a tightly-knit brother-and-sister pair who've grown up to become the best of friends. But between their jobs and spending their nights hanging out with one another at home, they've hardly had the chance to socialize with anyone else, a situation they want to put a stop to immediately. In no time, Gray and Sam have a chance encounter in the park with a striking beauty named Charlie (Bridget Moynahan). She catches Sam's eye right off the bat, and he falls so instantly in love with her that he proposes marriage which she surprisingly accepts. There's just one little problem: Gray is also in love with Charlie, a dilemma that worsens when the two women briefly but passionately kiss the night before Sam's wedding. Gray understandably freaks out and tries to make sense of these new feelings washing through her, but for her own sake, she has to make the tough decision of whether to ensure her brother's happiness or stay true to her heart. Graham and Cavanagh are certainly spirited performers with charm to spare, but the closeness of their characters is difficult to accept and even a little creepy. Heather Graham does look better than she's ever looked before but yet again she fails to pull her role off. Try as she might, in different genres, Graham just never manages to fool anyone that she's not acting. Tom Cavanagh is slightly more successful while Bridget Moynahan, as gorgeous as she is, also comes off as a little vacant. The film's great strength is it?s use of authentic New York locations, a necessity in any romantic comedy. Try as it may, Gray Matters doesn't have the charm or wit to pull it off. It's all one big misjudgment to be honest. The writer and director made the film about and for her sister and one gets the feeling that they may be the only ones who truly enjoy it.