Synonym: bankrupt, destitute, down-and-out, poor. Similar words: openness, pitiless, guileless, merciless, mercilessly, funnily, tennis, kenning. Meaning: ['penɪlɪs] 
adj. not having enough money to pay for necessities.
adj. not having enough money to pay for necessities. 
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1. He died penniless in Paris.
2. The legal dispute left them penniless.
3. Jobless and penniless ,(sentencedict.com) he had to sleep rough in the fields for several months.
4. Alone now and almost penniless, he was bereft of hope.
5. She fell in love with a penniless artist.
6. Uncle Charlie was jobless and penniless.
7. He found himself penniless in a strange city.
8. Laura found herself virtually penniless.
9. The penniless author successfully wooed and married Fanny.
10. They'd soon be penniless and homeless if she couldn't find suitable work.
11. Alone and penniless, I was forced to live on my wits .
12. She died penniless and was buried in an unmarked grave.
13. Ruling over these penniless black workpeople was a society of cultivated, well-mannered whites, a powerful colonial aristocracy.
14. She died penniless, in 1951[sentencedict.com], of liver and heart failure.
15. He died penniless, with over ￡17,000 owing to him, on 27 December 1650, unable to pay his doctor's bill.
16. He was broke, stranded, and penniless, and pleaded with Mum to send him his return fare money.
17. A fatherless, penniless boy - possessed of great determination, faith, and courage - seeks his fortune.
18. A group of deaf people were left penniless after their holiday was cancelled.
19. As penniless brokers they often had to dissipate energy on make-do and mend activities.
20. When the family came here from Russia, they were penniless.
21. He lived well, helping the poor, and all other people; he died penniless and unknown.
22. Because of her medical and her legal bills, she is now penniless and deeply in debt.
23. In the late Fifties and early Sixties these proved irresistible to a group of penniless artists looking for space for free.
24. But despite the vast amounts he earned in his career, Hunt was reportedly penniless at the time of his death.
25. She says she's highly embarrassed, but the alternative is being homeless and penniless.
26. Now there's Dan Crawley in hospital with the pneumonia, and poor Jenny is penniless by all accounts.
27. I had reached their house late at night from the train station, absolutely penniless.
28. If you will have it, yes, there were debts that did not permit of my marrying a penniless girl.
29. Serious inroads had now been made into my pitiful cash reserves and tomorrow I would be penniless.
30. My father was always desperately sorry for these jobless, penniless people, especially those who were ex-service men like himself.
More similar words: openness, pitiless, guileless, merciless, mercilessly, funnily, tennis, kenning, perennial, biennial, millennia, senile, table tennis, centennial, millennium, juvenile, bicentennial, nile river, pen name, pennant, juvenile delinquent, juvenile delinquency, carelessness, uselessness, selflessness, tactlessness, recklessness, hopelessness, homelessness, faithlessness.