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Advice: When does online flirting go too far?

Anna Pulley, @annapulley

RedEye's sex columnist

9:19 AM CDT, September 5, 2013

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I've been flirtatiously g-chatting with a co-worker of mine. He's married and even though I think (I know) I would never ever do anything, is this the way affairs start? Am I fooling myself? When does online flirtation cross the line to being not OK?—Emoticonfused

That line gets crossed probably around the time you start writing to a dating columnist asking whether you're crossing the line.

Flirtation in and of itself isn't harmful, Emoticonfused. We do it to blow off steam, to kill time at a boring job, to stave off the crippling loneliness of existence, etc. Most of the time, it's not a big deal at all. Other times, however, you're having an innocent chat about twerking and the next minute--bam!--you're naked and covered in edible body paint at a Super 8 outside of Naperville.

It happens to the best of us, even those who don't work at truck stops.

A good litmus test for whether your g-chats are sliding into dangerous territory is to ask yourself how you would feel showing them to your co-worker's wife. If the chats are harmless, then you should feel little to no guilt or anxiety at the thought of his partner seeing them. Or your partner, if you have one. If reading that just now caused you to make a wincing face, it may be time to take those conversations down a notch or take a step back altogether. Avoid innuendos and anything that might lead to emoticoncealment, or, worst of all, emoticontraception. Stick to neutral territory, like the coffee foam you just Instagrammed or your co-worker who's always speaking Portuguese to the fax machine. If all that fails, you could try actually working for a change too.

It is difficult to say precisely where affairs start, but it's probably somewhere around Schaumburg. Either that, or when it starts to feel "wrong." Does it feel wrong? Even if you would "never ever" do anything about it? If so, rethink your behaviors and what’s motivating them. If not, then you're probably fine. I think most of us know intuitively when we're making a bad decision, even if we go ahead and make the bad decision anyway. I feel that way every time I walk into a Chipotle.

Be sure you’re checking in with yourself frequently, and also maybe avoid anyone going by the name “Carlos Danger.” If nothing else, then seriously, girlfriend, get the strawberry-flavored body paint. It is off the hook.

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