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flirt with (someone or something)
1. To interact with someone in a way that shows romantic or sexual interest. I think Stacy's boyfriend was flirting with me at the bar. Should I tell her? After flirting with each other for months, Dan and Mary are finally going on a date.
2. To consider something, especially briefly or without earnestness. The business tycoon has flirted with running for public office for many years, but has yet to pursue it. I've been flirting with the idea of moving to Europe lately. I would need to save up a bit more money to make it happen, though.
3. To come very close to some outcome or result, often (though not always) a very bad one. The CEO has been flirting with disaster with her off-the-cuff comments to the press lately. The up-and-coming golf pro has flirted with success over the past few years, but he's yet to manage a major tour victory.
See also: flirt
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.
flirt with someone
to tease or trifle with someone alluringly. Are you flirting with me? Everyone knows that married men aren't supposed to flirt with anyone.
See also: flirt
flirt with the idea of doing something
Fig. to think about doing something; to toy with an idea; to consider something, but not too seriously. (See also flirt with someone.) I flirted with the idea of going to Europe for two weeks. Jane flirted with the idea of quitting her job.
McGraw-Hill Dictionary of American Idioms and Phrasal Verbs. © 2002 by The McGraw-Hill Companies, Inc.