The term 'Glass Half Empty Sort' is a phrase used to describe someone who has a pessimistic outlook on life. The crossword solutions for this term are 'DEFEATIST' (9 letters) and 'CYNIC' (5 letters). A DEFEATIST is someone who believes that they will fail or that their efforts will not be successful, while a CYNIC is someone who distrusts the motives of others and believes that people are generally selfish and untrustworthy. Both terms refer to people who have a negative outlook on life.