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c.1300 (late 13c. as a surname), from Old French jolif "festive, merry, amorous, pretty" (12c.) of uncertain origin (cf. Italian giulivo "merry, pleasant").
Perhaps a Germanic loan-word from a source akin to Old Norse jol "a winter feast" (see yule), or from Latin gaudere "to rejoice," from PIE *gau- "to rejoice" (see joy). For loss of -f, cf. tardy, hasty. Related: Jollily; jolliness.
To cajole with humor and bonhomie: I was pretty upset, but she jollied me along/ We jollied her into coming along with us (1876+)