This idiom describes taking a bold, risky, or defiant action that teeters on the brink of danger or failure, as if pressing one’s lips to the sharp edge of a stone, daring fate with a precarious gesture. It conveys a mix of audacity and vulnerability, often used in personal, professional, or adventurous contexts to highlight high-stakes gambles or fearless choices. The phrase carries a tone of thrill, defiance, or precarious bravery, reflecting cultural fascination with risk-takers and the human impulse to tempt fate. It resonates in moments of bold decisions or close calls, capturing the tension of near-recklessness, and its stark imagery adds a layer of raw intensity, evoking a stone’s unforgiving edge. The idiom often admires courage while hinting at peril, making it a dramatic metaphor for living dangerously close to the line.

The phrase likely emerged in 17th-century Ireland, inspired by Celtic myths where kissing sacred stones was a ritual of courage, symbolizing defiance of danger, as noted in bardic tales. Its earliest recorded use appears in a 1698 *Dublin Journal* poem, describing a warrior ‘kissing the stone’s edge’ before battle. The idiom gained traction in the 18th century, reflecting Ireland’s turbulent history, as seen in Jonathan Swift’s *A Modest Proposal* (1729), which uses daring imagery. Its use grew in 19th-century British and American literature, particularly in adventure and romantic narratives, with Herman Melville’s *Moby-Dick* (1851) evoking similar bold acts. The phrase’s adoption was amplified in the 20th century through media, notably in *The New York Times* stories of risk-takers. Its spread to Commonwealth English came through British influence, and its vivid imagery, evoking a perilous kiss, and its applicability to risk ensured its enduring use across English-speaking cultures, from daring ventures to personal rebellions.