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 After the sudden death of her fiancé, Gray Wheeler (Garner) finds comfort in the company of his friends: lighthearted and comic Sam (Kevin Smith), hyper-responsible Dennis (Sam Jaeger), and, oddly enough, his old childhood buddy Fritz (Timothy Olyphant), an irresponsible playboy whom she'd previously pegged as one of the least reliable people in the world. As secrets about her supposedly perfect fiancé emerge, Gray comes to see new sides of the man she thought she knew, and at the same time, finds herself drawn to the last man she ever expected to fall for.
Gray Wheeler (Jennifer Garner) thought she had life all figured out: the perfect job, the perfect city (Boulder, Colorado), and best of all, Grady, the perfect fiancé. However, in life, nothing is perfect: the day that was supposed to be their wedding day instead becomes Grady's funeral. At the memorial, Gray is comforted by Grady's closest friends: cheerful Sam (Kevin Smith) and responsible Dennis (Sam Jaeger).
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