One Question You MUST Ask Before Having Sex To Avoid Regrets

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Back in the dog days of the late 80s, when I started “dating”, I didn’t ask many questions before jumping into bed.

Granted it was another place, another time — a more innocent time — but not totally innocent; before the internet, but also after AIDS.

It was the end of high school for me, and while I was technically “sex educated”, I was also extremely horny and emotionally naïve. While these are not crimes separately, together they can be lethal. While I got my heart smashed into smithereens repeatedly (“Smashed Into Smithereens,” The Susanna Brisk Story) I did not die. Nor did I get the gift of a lifelong STD.

Luckily, you can’t catch Stupid.

After my first big broken heart, I took a vow of celibacy for six months, until a particularly charming actor swept me off my proverbial feet — literally from the stage. From then on, in the heady days of the 90s, I jumped into bed with people serially.

Did I want the person? Yes.

Did they want me? Yes.

After we had sex, would we then be “going out?”Yes.

I was a serial monogamist for three months to three years at a time. Then I would get rid of them when the next Shiny Love Object came along, because if that first broken heart had taught me one thing, it was that I wouldn’t be enduring that again. Getting dumped, that is.

Then I met my soon-to-be-husband, one-day-to-be-ex-husband.

We had a good run, and for the duration of the relationship, I shifted my life-focus off sex and onto other values — like trust, compatibility and laughter. Good values to be sure, but as a sensual person, I ignored our fundamental sexual incompatibility at my peril. In the marriage, I got the dad I always wanted, but not theDaddy I always wanted too.

After 14 years of (mostly) bliss, the whole thing appeared to be wedged apart by another penis, but the truth was far more complex. For No Penis Can Cast Asunder What Was Not Already Undone (Leviticus 3:12).

Since returning to the world of “dating” post-invention of the internet — though not Post-AIDS — certainly post-irony and post-wait-are-we-in-a-relationship-now-or-what-is-this-exactly-I-know-we-hooked-up-once-but-then-I-didn’t-hear-from-you-for-a-week-and-now-you’re-texting-me-at-11 p.m.-on-a-Wednesday … I have had to — to put it mildly — adjust. For in this time and place (Los Angeles, late summer, although I suspect also in other places and times) while nothing is assumed, much is still unspoken.

When looking for “The One” to move with behind the white picket fence I thought I wanted, I only asked these questions:

What do you do?

Where did you grow up?

Do you want kids someday?

What do you think of the Violent Femmes? (This last one was crucial.)

I see many young women still asking these things, and while they are valid (What do you think of Nickelback? is now particularly salient), they don’t get to the crux of the matter.

Post-divorce, the questions I started asking before jumping (discriminatingly) into bed — now that I no longer believe in either “The One” or “the fence” were:

What’s your name?

What generation were you born into?

What are you into?

When was the last time you were tested?

How did your last relationship end? Have you ever been in one? Can you have one?

Been married? Got kids? Want more?

How was your last sexual experience? Are you into monogamy?

Are you happy? What is the craziest thing you wouldn’t want me to know about you?

All solid questions — knowing that people lie, that people want to get laid (women too, silly), and certainly someone is capable of misleading you, but if you keep it in your pants for a second, our short post-internet attention spans dictate that usually people run out of energy for deception.

But what I have found is MOST important, the question that in the last 6 months has saved me SO much heartache and headache and lonely is this: 

What are you available for?

And then watch. Not only watch, but also observe. Take mental notes. See the behavior — not just the words — the breath and the pupils dilating (they do that with desire). Undertake a curious, scientific exploration of What This Person Can Share With You At This Time.

Not what they wish they were up for. I have had 22-year-old men tell me with absolute gravity they wanted to be my “boyfriend,” and 52-year-old men assure me they were fine with non-monogamy, but what are the facts? How often do they call and text? Do they show up when and where they said they would, even when sex is not yet on the table? How does your body feel in their presence? Do they feel entitled to sex or will they wait to figure it out with you? Do they make snide remarks? Do they make you feel tired?

Pay attention, for sooner rather than later, people will reveal exactly who they are, simply by showing you what behaviors they can sustain.

The amount of bandwidth they have will be obvious shortly if you can just keep your pants zipped a little while longer. And believe me, if I can do it (Horniest Girl Of The Year 1988-present), you can too.

If casual sex is what you are after, please have at it — sometimes it can be just the palate cleanser the doctor ordered. But be clear that that is what it is and do not waver in that clarity. If you want more, there is no substitute for consciously and methodically getting to know someone before you release the hounds of Oxytocin and everything goes to holy heaven/hell.

And before posing that question above to someone else, here is the ultimate kicker: post that question to yourself.

What am I really available for? (Add that REALLY, just to make sure you are paying attention.)

Don’t try to fake yourself out with flowers and pronouncements and grand ideas of what youshould want because of your age, or race, gender, or some other thing. These may all be mitigating factors, but they are not decisive. Who are you and what do you want? Who are you going to have to be to get it? Who makes you happy? (Never Why, because that part is always a mystery…)

Before beginning a negotiation with anyone for anything, you must start by being absolutely honest with yourself — authentic, audacious, and flexible. Find out what you want and need, in this moment in time, and then go after it with everything you have, by asking specifically in every moment for what you want and need, without manipulation or agenda — though certainly charm is fine.

Do not settle. Keep in mind that you are not entitled to anything from anybody — not the relationship of your dreams, not dinner, and certainly not gasp! sex. Sit down, look ‘em squarely in the eye, and fight for your true soul’s expression.

Order your coffee how you like it and then plant your feet and ask the magical question, “What are you available for?”

And wait.

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