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.

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: