Might mean (unverified): Persistent failure to achieve success.
Definitions Related words Mentions
We found 2 dictionaries that define the word loserness:

General (1 matching dictionary)
  1. loserness: Wiktionary

Slang (1 matching dictionary)
  1. loserness: Urban Dictionary

Definitions from Wiktionary (loserness)

noun:  (slang) The quality of being a loser.

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