Break the ice
"To ease initial social tension or awkwardness, especially between strangers."
Before icebreaker ships, frozen harbours and rivers could completely cut off a town from trade and travel. Small boats specially reinforced to break a path through surface ice were sent ahead to open the way for other vessels, a literal "breaking of the ice" that let normal business resume. Writers were using it figuratively, for smoothing over the "frozen" awkwardness of a first meeting, as early as the late 1500s.
Sources: Figurative use documented from the late 16th century, cited in the Oxford English Dictionary's entry for 'ice, n.'
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