Wise Guys: Is There Such a Thing as Harmless Flirtation?

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Advice from three of our guy friends. This week a woman asks, “Is there such a thing as harmless flirtation? When does it cross the line? Is the line different for men and women?”

wiseguy_benStraight Married Guy (Ben): Sure – there are plenty of harmless flirtations. Most flirtations, I think, are harmless. The question of line-crossing is really an individual one, determined by your partner (and yes, I think, generally, women do have lower tolerance for this than guys). Some people you date may think a simple flirt is a great betrayal. Others are really into open relationships. It’s a good thing to talk about with your partner cuz it’s important information on deciding whether or not this person is for you. My experience tells me that actions are more important than words and, to me, cheating is a physical act. But, you know, it doesn’t really matter what I think because, in my marriage, I’m not being faithful to myself – I’m being faithful to my wife. And to her ideas of fidelity.

Gay Married Guy (Jon Ross): Harmless flirtation is something that makes long term committed relationships work. I mean, c’mon, we’re human. In life, we do see other interesting, attractive people other than our boyfriend or spouse and we may feel like paying them a compliment. Of course, the point at which harmless flirtation crosses the line to harmful flirtation is different with each relationship. Some people are far more jealous and possessive than others and if there is a history of unfaithfulness, I would give my spouse little leeway. Also, there is a huge difference if the flirtation is going on while the other person is present. I couldn’t care less what happens when I’m not with my husband, but if we’re at a party and he’s ignoring me to chat it up and laugh with some hot daddy all night, there will be repercussions. I don’t think there is a different line for men and women — each person handles it differently.

anonymous_suitStraight Single Guy (Max): Flirtation is and should always be fun. When it becomes harmful, then I don’t think you can call it flirtation any more. The line, as far as I’m concerned, is pretty much anything physical. Words, no matter what they contain, are harmless until acted upon. Admittedly, I wouldn’t want to find text messages declaring a lover’s desire to do much of anything with anyone else, but then the question becomes whether or not you believe if they would follow through with any of the said declarations. Then things might get a little harmful. Until then, I encourage eye contact with beautiful strangers, sexy conversations with ladies at parties and as much co-worker flirtation as possible. Just keep your hands to yourself.

Our “wise guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Straight Married Guy is Ben, a writer and artist living in Los Angeles who runs AdultParlorGames.com; our Gay Married Guy is Jon Ross, who works for a network news program and lives in Brooklyn with his husband and two dogs; and our Single Straight Guy, Max, is a recent college grad in New York City. To ask the guys your own question, click here.


  1. For me the big issue is when it gets misread; “harmless flirting” gets misread as “she wants a relationship with me and is willing to leave her boyfriend to get it” or “she wants me to divorce my wife for her.” Believe it or not, this has happened to me.

    Just be very careful about intentions and how you communicate them; broken hearts and destroyed friendships happen a lot

  2. There is such a thing as an emotional affair. Too much flirting can lead to that. So, just know where the boundaries are.

  3. Hmmm… I don’t know. The sexual thrill I get from mutual flirtation is very real. It stirs my sanguine humors, you could say.

    You could say that this is harmless in itself, but once my sanguine humors head loinward the likelihood of an actual transgression skyrockets. I’m a thrill-seeker with poor impulse control. I do not stand up well to temptation. For this reason a lot of women who know me think of me as a non-sexual guy. I flip it off like a switch when I’m in a relationship. I am nice and polite and non-flirtatious with the women I know. I don’t want them thinking of me as a sexual possibility. That’s a slippery slope.

    So for me it’s like saying there’s harmless drunk driving – bullshit. Just because you didn’t crash doesn’t mean it was safe.

    But that’s just me. I fully believe that there are men and women out there who can flirt a little without winding up naked.

  4. My boyfriend and I are both flirts, but since we trust each other and know where the line is on where flirting can go, we don’t mind a bit of flirting with other people (and each other! That’s always fun).

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