Men and the Fine Art of Flirting (and the Decided Line for Harassment)

Take and use this advice from a serial flirter — from knowing your audience to taking a “no” like a pro.

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Photo Credit: iStock Photo

By Kara Post-Kennedy

First of all, you should know that I am a flirt.

I come from a long line of proud flirters; both of my parents could have gone pro. If you have never had the pleasure of watching people who have been flirting with each other for 50 years put the rest of us to shame with their mad skillz, my condolences.

It is an unparalleled experience.

But here’s the thing: I was raised by people who didn’t necessarily view flirting as sexual in nature. One definition of flirting is “to become involved in something in a way that is not very serious”; I see flirting as light-hearted banter, not a directive. We’ve all had the experience of a small child “flirting” with us (much to our delight), and in my family at least, flirting can be a default position in situations where we are uncomfortable. For example, my younger sister once famously (or infamously) winked at an admissions officer during a college interview.

Flirting can elevate the mood of an exchange, create a superficial bond in awkward situations or just be a plain old good time.

I grew up in an era where you never really heard about “sexual harassment” and it was not on my radar until Anita Hill made it headline news in 1991. I was just out of college, working at restaurants in NYC where “flirting” was rampant. I quickly came to understand that there was a “line” that once crossed turned something innocent into something scary and potentially dangerous.

I recently had lunch with a dear old friend of mine who is a badass, high-powered advertising exec; listening to her talk about the modern-day office environment made me realize I’m a sexual harassment case waiting to happen. Between my sense of humor, my physicality (I’m a hugger!) and the fact that I get into personal, intimate conversations with strangers at the drop of a hat, I would not do well in corporate America.

When I was young, “flirting” versus “sexual harassment” was mainly about tone, environment and reciprocity; nowadays it is much, much more complicated. And fact is there is definitely a double standard because men generally are not threatened by women flirting with them (for obvious reasons). It made me start thinking about situations I and women I know have been in where our boundaries were being violated by someone who considers themselves innocuous.

I will try to provide some handy guidelines for respecting feelings and limits; these are questions men can ask themselves to understand the difference between a harmless behavior and a threatening one:

Are you a legal adult flirting with someone who has not yet reached the age of consent?

Because that is textbook sexual harassment. I understand there are borderline situations (you just turned 18! You want to boost the self-esteem of an insecure kid!) but there are laws protecting minors for good reason. There is not a woman I know who was not the target of unwanted sexual attention as a teen (or YOUNGER) girl by an adult man. Pick on someone your own size.

Or don’t, actually.

Are you in a position of authority over the person you are flirting with?

Again, this is sexual harassment, even if it is reciprocated. First of all, you have no clue if it is reciprocated because the person fears for their job and, secondly, if you are flirting with one subordinate and not another, it can make for a very tense and/or hostile work environment for them both. Just say no.

Are you using language that is demeaning or diminutive?

Demeaning language is harassment, plain and simple. Ditto for catcalls or even (this has happened to me too many times) talking about women in a sexual or demeaning way in front of other women. Just because you are not specifically referring to ME as a “piece of ass” doesn’t mean I am not offended to hear you use this terminology. I am not “one of the guys” and you frankly have diminished yourself in my eyes by saying these kinds of things. Speaking of diminishing, if your “flirting” behavior strikes the note that I am “little”, “weak” or in need of your “services” — that’s harassment. Back off.

Where are you?

From what my friend was telling me, flirting in the workplace even with a co-worker who is your “equal” is pretty much frowned upon. Any kind of touching, even to get someone’s attention, can get you hauled into HR. So as a rule of thumb again, just say no. Bars basically exist so we can get our flirt on, but here is also the place where we all need to USE and HEAR the words “no thank you.” If flirting is not welcomed/reciprocated, it is sexual harassment. I am a hugger, as I mentioned; I once hugged a stranger in a bar, but only AFTER he hit on me, thereby expressing interest. I rejected him, but then hugged him because he was sweet and respectful about it (lots of good guys out there). I also hug people in church constantly, but it’s a VERY huggy kind of church.

Basically the overall message here is to know your audience and respond to cues (and words!!!)

What is the nature of your relationship?

This should be a no-brainer, but sadly it is not.

We all have long-term entrenched relationships that do not involve sex but DO involve flirting. Again, flirting in and of itself is not sexual, any more than admiration or appreciation is. Also, we all have a “tolerance level” when it comes to flirting; mine is very high and I rarely feel offended or threatened, but I do NOT impose my personal boundaries on others. Most of us flirt with people we know well to some degree or another. It’s with those people with whom our connection is more tenuous (the neighbor you see a few times a year, the parents of other kids in your child’s class) that you need to tread lightly. Again, KNOW YOUR AUDIENCE and when it doubt, err on the side of caution.

What is your intent?

I am an equal opportunity flirter: man, woman, old, young, I am a flirter without borders! If you look pretty (or handsome) today, I will say so. If I like your dress, haircut, attitude, style, WHATEVER, I will mention this. I once pestered Mandy Patinkin in a NY restaurant, vomiting my admiration all over the poor man and excused my behavior by saying I decided it would be okay to interrupt his dinner because I always love when people tell me they think I’m wonderful. To which the great Mr. Patinkin replied, “Miss…I think you’re wonderful!”

FLIRT ALERT! Complimenting others not only boosts their mood, but it also boosts yours as well. If this is your intent and you will happily go about your life once the compliment has been received, then you are flirting. If you are hoping that “nice dress” will influence her into taking it off? Unless you are in an established relationship, that is harassment. We can tell the difference between a sincere compliment and a come-on, btw. Dial it back.

So there are some basics to help you negotiate the minefield of flirting in modern society. Most important takeaways: know your audience, err on the side of caution and accept the phrase “no thank you”. But I have one parting thought I would like to throw out there, this one for the women:

We have all experienced harassment; many of us have experienced some kind of assault or abuse at the hands of a man. It is okay to be guarded around men you don’t know, don’t like or don’t trust. But I do think it is useful to remember that “innocent until proven guilty” is the linchpin of our legal system for a reason.

Most men, even when hapless, are not ill-intentioned. If he doesn’t take “no” for an answer, then he is a danger. Otherwise, he is just a guy trying to figure things out. Maybe you can help him do that instead of simply shutting him down. His response will give you all the information you need.

This story was previously published on The Good Men Project.

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