/ Dictionary / Index T two-time loser: Meaning and Definition of Find definitions for: two'-time los'er Pronunciation: [key] — Slang. Slang. a person who has been sentenced to prison twice, esp. for a major crime in a state where a third sentence is mandatory life imprisonment. a person who has failed at the same endeavor twice. Random House Unabridged Dictionary, Copyright © 1997, by Random House, Inc., on Infoplease. two-time two-toed anteater Related Content Daily Word Quiz: resilient Analogy of the Day: Today’s Analogy Spelling Bee: Today’s Spelling Bee Frequently Misspelled Words Frequently Mispronounced Words Easily Confused Words Writing & Language