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2.
1) Combination: pillows + philosophy

2) The study of general and fundamental problems concerning matters such as existence, knowledge, values, reason, mind, and language just before one falls asleep.

3) The rational investigation of the truths and principles of being, knowledge, or conduct before dreaming.
"I went to bed and found my pillosophy."

"While I was pillosophizing last night, I remembered that the next day was my spouse's birthday."
by JWSTigre February 23, 2010
 
1.
To contemplete the most fundamental and general concepts and principles involved in thought, action and reality while under the influence of narcotics.
Mike spent half the night stretched out on the back lawn discussing foreign film, personal problems and Pillosophy with someone he’d only just met.
by Paul_A January 02, 2007