Gray (Heather Graham) and Sam (Tom Cavanagh) are as close as people can be. They are best friends, roommates and siblings. They are so close that people mistake them for a couple often and while the back of the DVD says that they are brother and sister, the director feels the need to make us believe they are dating at first, so we will be a bit shocked at the reveal of them being related. Gray cannot seem to find the man of her dreams and all of her friends believe it is because she and Sam are incredibly too co-dependant. Sam can't find the girl of his dreams because he is working on his residency at a hospital becoming a heart surgeon. They agree they need to help each other find someone and Gray is quick to find Sam a gorgeous wonderful woman, Charlie (Bridget Moynahan). She is so perfect for Sam that he proposes after one night and they are planning to fly to Vegas to get married that weekend. Because it is so rushed, they ask Gray to be their witness and at first we see that Gray is jealous Sam has found someone so perfect, but soon we come to think maybe she is jealous for a different reason. The night before the wedding Sam is not a lot to see the bride so Charlie and Gray hang out for the night- taking a bath together, singing on stage with Gloria Gaynor and getting absolutely hammered. At the end of the night, they share a long passionate kiss. The kind of kiss that can make one question everything one believes and that is exactly what happens to Gray. Charlie seems to have no recollection of what happened but Gray harbors this secret, although she does not say anything to Sam about it.
What happens for the rest of the movie is Gray trying to come to terms with the possibility of being gay. She is in love with Charlies, that is obvious, but is she gay? Is she just reacting to her brother finding eternal happiness? Was the kiss just that good? This is the crux of the movie and along for the ride are the pointless Sissy Spacek as an awful therapist, the always obnoxious Molly Shannon as Gray's best friend and the incredibly sweet and charming Alan Cumming as a cab driver harboring a giant crush on Gray. Gray tries to go on dates with men and she tries to forget Charlie entirely but nothing seems to work. Eventually she tells Sam what happened and he reacts by cutting Gray from his life. Because it is a whimsical romantic comedy featuring two classy dance numbers, everything comes out alright in the end and we do realize that yes, this is a coming out film, but sadly, it doesn't end there. In the final 10 minutes it tries to turn into a gay rights film as Gray spouts off this diatribe about how she is lonely because she'll never be able to get married or hold hands without people whispering. Now there is nothing wrong with the sentiment in this film, because I agree with it all, but this ending feels forced, this movie is about one woman's transition into who she really is and becoming comfortable as a gay woman. It is not about gay rights!
I can't say I really enjoyed the movie much because Heather Graham is about the worst actress working. She is moderately charming and handles the sweetness alright, I guess, but she is simply just a hot actress who can't act. Tom Cavanagh is a charming and goofy actor who is wasted in a secondary role and it is a shame because he really is like Zach Braff, only a bit older (which is why he plays Braff's brother on Scrubs). Moynahan is gorgeous charming and funny and it is easy to see why everyone in this thing falls in love with her. The writer director seemed hell bent on turning this into some gimmicky sitcom, complete with a pointless cross dressing moment, for laughs I guess. I like the idea and the basic structure of the movie, but perhaps with a better lead, better script and more capable director this could have been worth the 90 minutes of my time.
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