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It can be difficult to tell if someone is flirting with you, even on a good day. People get nervous, they try to "play it cool," and some simply lack the. How To Tell If A Guy Likes You At Work [Flirting Signs] . Never mistake this for typical office chit-chat—it's veering into the personal and it's a clear attempt to. If he's chatting up everyone in the office, he's probably just a social butterfly. But if he talks to you . over the line. MORE: Signs He's Definitely Flirting With You.