verb (used without object)
to court triflingly or act amorously without serious intentions; play at love; coquet.
to trifle or toy, as with an idea: She flirted with the notion of buying a sports car.
to move with a jerk or jerks; dart about: butterflies flirting from flower to flower.
verb (used with object)
to give a sudden or brisk motion to; wave smartly, as a fan.
to throw or propel with a toss or jerk; fling suddenly.
Also, flirter. a person who is given to flirting.
a quick throw or toss; sudden jerk or darting motion.

1540–50; expressive word; compare similar initial cluster in flap, flick1, flip1, and final elements of squirt, spurt, etc.

flirtingly, adverb

1. tease. 1, 2. dally. 6. minx, coquette, tease. Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2014.
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World English Dictionary
flirt (flɜːt)
vb (usually foll by with) (usually foll by with)
1.  (intr) to behave or act amorously without emotional commitment; toy or play with another's affections; dally
2.  to deal playfully or carelessly (with something dangerous or serious); trifle: the motorcyclist flirted with death
3.  to think casually (about); toy (with): to flirt with the idea of leaving
4.  (intr) to move jerkily; dart; flit
5.  (tr) to subject to a sudden swift motion; flick or toss
6.  a person who acts flirtatiously
[C16: of uncertain origin]

Collins English Dictionary - Complete & Unabridged 10th Edition
2009 © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins
Publishers 1998, 2000, 2003, 2005, 2006, 2007, 2009
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Word Origin & History

1550s, originally "to turn up one's nose, sneer at," then "to rap or flick, as with the fingers" (1560s). The noun is first attested 1540s, with the meaning "stroke of wit." It's possible that the original word was imitative, along the lines of flip (v.), but there seems to be some influence from flit,
such as in the flirt sense of "to move in short, quick flights," attested from 1580s. Meanwhile flirt had come to mean "a pert young hussey" [Johnson] by 1560s, and Shakespeare has flirt-gill (i.e. Jill) "a woman of light or loose behavior," while flirtgig was a 17c. Yorkshire dialect word for "a giddy, flighty girl." All or any of these could have fed into the main modern verbal sense of "play at courtship" (1777), which also could have grown naturally from the earlier meaning "to flit inconstantly from object to object" (1570s), perhaps influenced by O.Fr. fleureter "talk sweet nonsense," also "to touch a thing in passing," dim. of fleur "flower" and metaphoric of bees skimming from flower to flower. The noun meaning "person who flirts" is from 1732. The English word also is possibly related to E.Fris. flirt "a flick or light blow," and flirtje "a giddy girl." Related: Flirted; flirting.
Online Etymology Dictionary, © 2010 Douglas Harper
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Example sentences
Brightening his colors and flirting with different styles didn't seem to help.
The temperature outside was flirting with sub-zero temperatures, but hundreds
  of people lined up early to get in.
The former is still flirting with economic and political collapse, the latter
  has simply exploded.
Organizing or attending protests gets fitted between flirting, studying, and
  holding down a job.
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