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Answer:
OPTIMIST
Possible Questions:
One perpetually full of hope
One with high hopes
Hopeful soul
Glass-half-full person
Sanguine one
Rose-colored glasses wearer
Prisoner of hope
One with rose-colored glasses
One with a positive outlook
Murphy, per O'Toole
His glass is half full
Distinguished Canadian service club member
"A guy that has never had much experience": Don Marquis
'Half-full' believer