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We’ve been describing a man who is a kind, thoughtful person as a聽nice guy聽since at least the early 1900s, as far as the written record is concerned.聽Nice fellow predates it, evidenced in the early 1800s.

His reputation, though, hasn’t aged well. Nice guy聽has become a stand-in for a loser, particularly in dating contexts.

He shows up in the saying聽nice guys finish last鈥�agreeable people who get overpowered by their more assertive counterparts鈥攚hich is credited to Brooklyn Dodgers manager Leo Durocher in 1946. He famously dissed the New York Giants that season when he said of their near-bottom standing: “The nice guys are all over there, in seventh place.” Reporting eventually rendered the quote into nice guys finish last.

Nice guy also makes an appearance in no more Mr. Nice Guy, said when someone is throwing down鈥攁nd implying nice guys are soft and weak. Alice Cooper rocked the saying in his 1973 track “No More Mr. Nice Guy.” A reporter memorably asked it of Richard Nixon about the Vietnam War in 1977. No more Mr. Nice Guy is also associated with an old joke about Hitler.

When nice guy makes the jump from sports, politics, and rock ‘n’ roll to romance isn’t exactly clear, but the expressions聽nice guys finish last and no more Mr. Nice Guy聽certainly contributed to the trope of the nice guy鈥�a perfectly harmless dude who is just, well, kind of uninteresting and unappealing.

Since at least the late 1980s, as evidenced in an early internet-message group, romantically unsuccessful men have self-identified as the nice guy, always losing out to the bad boy. In the 1990s and early 2000s, sociologists were even using聽nice guy, in one form or another, as a concept when studying dating behavior and psychology. Their findings show that nice guys聽do indeed finish last鈥攊n some cases.

What gives? You’re a nice guy, but … your kindness is masking some serious insecurities, if not expecting it to be rewarded with sex. At least that’s in part how the website Heartless Bitches International聽saw it in their 2002 screed against the nice guy.聽In the feminist blogosphere in the 2010s, the screed helped influence Nice Guy鈩⒙�and Nice Guy Syndrome, terms for men who think being nice alone entitles them sex. The manosphere had its answer, including incels and Men Going Their Own Way, subcultures who blame women for their romantic and sexual failures.

Not all men have taken criticisms of the contemporary nice guy so self-seriously, though. Hundreds of thousands belong to the subreddit r/niceguys, intended to make fun of nice guys who fail to take responsibility for their own shortcomings.