Plot
Gray Baldwin (Heather Graham), a family oriented and quiet bachelorette, lives a close-knit life with her brother, Sam (Tom Cavanagh). Their lifestyle is generally co-dependent, involving them living together, going to dance classes together, etc. Gray and Sam's relationship has never been thought of as strange, but once a dinner party guest mistakes the siblings as a couple, Gray and Sam decide to venture outside of one another. While discussing with each other what they can do about their single lifestyles, and how they can "hook each other up" with a significant other. Their conversation continues to the park, where Gray meets a possible girlfriend for Sam, Charlie Kelsey (Bridget Moynahan). Gray then introduces Charlie and Sam, and they instantly bond, agreeing to see each other again.
To Gray's surprise, Charlie and Sam become engaged, two days after their meeting. Charlie and Sam insist they are so in love with one another, they should go to Las Vegas the following morning and elope there, inviting Gray along. Gray is a little hesitant, but agrees when Charlie says they can have a "mini bachelorette party". Gray agrees and the three make their way out to Vegas. While in Vegas, Gray takes Charlie out for a hen night, and after many drinks, the two share a drunken kiss. The next morning, Charlie does not remember anything, but Gray has not slept the whole night, due to the bond she felt with Charlie. After realisation, Gray comes to a conclusion that she is attracted to women, and is falling in love with her sister-in-law.
The events that occurred in Vegas begin a beautiful journey of self-discovery, testing the relationship between two close siblings and finding happiness in lonely Manhattan.
Read more about this topic: Gray Matters
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—Ralph Waldo Emerson (1803–1882)