If someone is said to be "Chasing the dream" Its means that they are going out drinking again on the night after a previous nights heavy drinking, even though they know it wont be as good as the previous night. An example would be having an amazing night on a Friday, then on the next day (saturday) going out again, trying to replicate the previous nights antics. They are said to be "chasing the dream"
Guy 1: You going out again tonight?
Guy 2: Yeah, think it will be really good.
Guy 1: I think you are chasing the dream.
Guy 2: Yeah, think it will be really good.
Guy 1: I think you are chasing the dream.
by big-cigar January 22, 2012