Penniless/ˈpeniləs/ Definition 1 of 1Pro Tip 1/3Emotional Weight The term evokes sympathy or sadness, suggesting extreme poverty or misfortune. Once a wealthy man, now he roams the streets penniless. Pro Tip 2/3Not Just Broke 'Penniless' often implies a lack of resources beyond just money, like support or assets. She found herself alone and penniless in the city. Pro Tip 3/3Temporary State Can refer to a momentary situation, not necessarily a permanent condition. After paying all the bills, I'm penniless until payday.