A group of contest winners arrive at an island hotel to live out their dreams, only to find themselves trapped in nightmare scenarios.

Peter Klaven is a successful real estate agent who, upon getting engaged to the woman of his dreams, Zooey, discovers, to his dismay and chagrin, that he has no male friend close enough to serve as his Best Man. Peter immediately sets out to rectify the situation, embarking on a series of bizarre and awkward "man-dates."

A man is broken hearted at the loss of his lover, then later visits the same pain on the next woman with whom he becomes involved.

After the death of his mother, a man tries to discover a meaning to his life, to the universe and to rebuild a relationship with the only family he has left: his gay brother.