How Do I Tell If It’s Flirting For Fun Or Flirting For Real?

I seem to have lost the knack of flirting frivolously and freely and devil-may-care.

There’s a woman I keep running into at gatherings far and wide, and I’ll be honest, part of my problem is that I find her distractingly hot, but she’s married (to a man) and I don’t know if she’s queer or poly, and I don’t know her well, and it’s all very fraught because either she’s just flirtatious with everyone, or flirtatious with me but without intent, or aiee, I’m afraid to ask clumsily and find out I guessed wrong.

Help me, Bitter Butch, you’re my best hope! How do I ask her what’s up without making things horrible if it was all meant to be funsies?

Fretfully Flirting

Dear FF:

Some people just love flirting, and I think she’s one of those people.

The reason I believe this is that if a woman is married to a man and wants to have a relationship with someone else, male or female, it’s up to her to make the first move. Our society defaults to monogamous, and unless you met her at a Queer Poly Meetup, she knows that it’s up to her to break the ice if she indeed wants a relationship (even a one-night relationship) with you.

If you want to be sure that you mark yourself as someone safe to hit on, you can certainly mention being poly (if you are poly), or being interested in non-monogamy, or just in general chat about it as a concept and show that you are open-minded on this topic.

That said, telling her that you’re interested is not a nuclear bomb. Asking her what’s up doesn’t have to be horrible if the answer is: oh! I’m just a flirt.

Is there something impossible about saying: “You are such a flirt! Do you mean it, or are you just having fun?” That is a real question; some people find such directness utterly agonizing. If you can’t, you can also just say: “You are such a flirt!” and wait to see if she expands on that statement.

I’m always sort of mystified by people who think they will ruin friendships forever by asking someone if they make them feel a little funny in their underpants. If someone mentions it, or asks someone else out, and that person says no thank you, and then you all move on, what is it more than a small moment of awkwardness?

This letter originally appeared in bitterempire.com on August 20, 2015.

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