1570s, "behavior of a courtier," from court (n.) + -ship. Meaning "the wooing of a woman, attention paid by a man to a woman with intention of winning her affection and ultimately her consent to marriage" is from 1590s. By 1830s it was used of a period during which a couple mutually develops a romantic relationship with a view to marriage.
The main modern verbal sense of "play at courtship" (1777) probably developed from the noun (see flirt (n.)) but also could have grown naturally from the 16c. meaning "to flit inconstantly from object to object." To flirt a fan (1660s) was to snap it open or closed with a brisk jerk and was long considered part of the coquette's arsenal, which might have contributed to the sense shift. Or the word could have been influenced from French, where Old French fleureter meant "talk sweet nonsense," also "to touch a thing in passing," diminutive of fleur "flower" (n.) and metaphoric of bees skimming from flower to flower. French flirter "to flirt" is a 19c. borrowing from English.
c. 1200, gelus, later jelus, "possessive and suspicious," originally in the context of sexuality or romance (in any context from late 14c.), from Old French jalos/gelos "keen, zealous; avaricious; jealous" (12c., Modern French jaloux), from Late Latin zelosus, from zelus "zeal," from Greek zēlos, which sometimes meant "jealousy," but more often was used in a good sense ("emulation, rivalry, zeal"), from PIE root *ya- "to seek, request, desire" (see zeal). In biblical language (early 13c.) "tolerating no unfaithfulness." Also in Middle English sometimes in the more positive sense, "fond, amorous, ardent" (c. 1300) and in the senses that now go with zealous, which is a later borrowing of the same word, from Latin.
Most of the words for 'envy' ... had from the outset a hostile force, based on 'look at' (with malice), 'not love,' etc. Conversely, most of those which became distinctive terms for 'jealousy' were originally used also in a good sense, 'zeal, emulation.' [Buck, pp.1138-9]
Among the ways to express "jealous" in other tongues are Swedish svartsjuka, literally "black-sick," from phrase bara svarta strumpor "wear black stockings," also "be jealous." Danish skinsyg "jealous," literally "skin-sick," is from skind "hide, skin" said to be explained by Swedish dialectal expression fa skinn "receive a refusal in courtship."
late Old English cæppe "hood, head-covering, cape," a general Germanic borrowing (compare Old Frisian and Middle Dutch kappe, Old High German chappa) from Late Latin cappa "a cape, hooded cloak" (source of Spanish capa, Old North French cape, French chape), a word of uncertain origin. Possibly a shortened from capitulare "headdress," from Latin caput "head" (from PIE root *kaput- "head").
The Late Latin word apparently originally meant "a woman's head-covering," but the sense was transferred to "hood of a cloak," then to "cloak" itself, though the various senses co-existed. Old English took in two forms of the Late Latin word, one meaning "head-covering," the other "ecclesiastical dress" (see cape (n.1)). In most Romance languages, a diminutive of Late Latin cappa has become the usual word for "head-covering" (such as French chapeau).
Meaning "soft, small, close-fitted head covering" in English is from early 13c., originally for women; extended to men late 14c. Extended to cap-like coverings on the ends of anything (such as hubcap) from mid-15c. Meaning "contraceptive device" is first recorded 1916.
Meaning "cap-shaped piece of copper lined with gunpowder and used to ignite a firearm" is by 1825, hence cap-gun (1855); extended to paper version used in toy pistols, 1872 (cap-pistol is from 1879).
Figurative thinking cap is from 1839 (considering cap is 1650s). Cap and bells (1781) was the insignia of a fool; cap and gown (1732) of a scholar. To set one's cap at or for (1773) means "use measures to gain the regard or affection of," usually in reference to a woman seeking a man's courtship.