means Without any chance of success, improvement, or relief — or describing someone so bad at something that improvement seems impossible.

from A transparent English build: "hope," from Old English "hopa" (expectation, trust), plus the suffix "-less," from Old English "-lēas" (free of, lacking) — the same "-less" that strips comfort from "comfortless" and ends from "endless." So at root it means simply "lacking hope," the word wearing its emptiness right there in its spelling. The breezier sense — "a hopeless cook," "hopeless at maths" — came later, hope quietly broadening from a feeling you've lost to a prospect you never had.