How deep should you get in conversation?

21 Sep

Some men have the misguided idea that when on a date, revealing as little of themselves as possible will create an attractive air of mystery. No surprise that their conversations always run cold quickly.

Others go the other extreme. I have a friend who’s good at reading others’ emotional cues and mental models–too good. He can always tell when you’re unsure or uncomfortable about a subject–and he will grill you at that point. “Really?” “What makes you say that?” “Tell me more!” Talking with him sometimes drives me nuts.

I’ve seen him do the same with strangers–they were literally squirming in their shoes.

There’s this school of thought that says men should have deep conversations with women as soon as possible.

Supposedly, women have tired of mundane, superficial conversations with shallow men. They would jump at the first opportunity to connect with a man who can enter in deep, intimate conversation. If you want to make an impression on women, make it your aim to have deep, meaningful conversation within 10 minutes of meeting a woman. Small talk is the province of novices–skip it! The expert can get straight to the good stuff with any stranger.

Years ago I read dating columns describing the following exercise for men: Walk up to people you’d never met before. Ask them, “So, what are YOU passionate about?” Sure, you’d get weird looks initially, but it’s just a matter of getting used to it and becoming comfortable.

I never put that advice to practice. It was just too hard. Not to mention that I couldn’t shake off the suspicion that I’d actually be screening for nutcases–which emotionally stable woman would pour their heart out to a stranger? (Of course, it might be a good idea if I were an out-of-job shrink canvassing for business.)

How deep, then, should you aim to take your conversations with women? Authentic World just gave a fantastic answer to this question: You should simply take your conversation to wherever it’s at.

Great conversation isn’t about “going as deep as possible”. It’s about being aware and open to whatever the situation is in front to you. To engage your partner at whatever level she’s willing and comfortable.

That means you shouldn’t shy away from revealing more of yourself when the opportunity arises–or when she’s interested to know.

It means you should not to force your way into deeper conversation when she’s not willing to, or uncomfortable. If the chemistry’s not there, don’t try to manufacture it. If you know it’s not there, she probably knows it’s not there either. At that point, conversation skills are not about “creating attraction”. It’s about civility, courtesy, and being social.

In other words, “small talk”.

You can’t lead a conversation in a date. Rather, the conversation leads you. Whatever the level your conversation’s at–superficial, intellectual, emotional–you need to accept it as it is. Celebrate every stage of the conversation for exactly what it is.

But what if conversation does get deep?

Deep conversation is about self-revelation and vulnerability, so discomfort must be managed. Here’s how:

If your date appears uncomfortable with a subject, don’t ignore it because it’s important for “the progress of the date” to “go deeper”. Acknowledge her discomfort. Let her decide whether she wants to talk about it.

If you’re the one uncomfortable with the direction of conversation, don’t pressure yourself (or feel pressured.) Admit your discomfort (she’s probably already noticed it), and explain the source of your discomfort. This admission alone will almost always lead to a deeper conversation, all by itself.

If you’re feeling attraction for her, just let it show. No, I don’t mean you should make a  showy confession. But don’t hide it either.

If you’ve positive feelings and you wish to express them, don’t qualify your words . Many men backpeddle at the first sign of sexual tension: “I hope you don’t take it the wrong way,” “I don’t mean anything special by that.” You think you’ve giving yourself a backdoor in case the date goes sour. You’re not. You’re weaselling, and you’re killing whatever attraction you’ve built up so far.

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3 Responses to “How deep should you get in conversation?”

  1. Phoebe September 22, 2011 at 9:33 pm #

    Interesting. Normally I back off if I feel I am touching on a touchy topic to the other person. I let him/her decide if he/she wants to continue in that area. Don’t know how deep the other party wants to go…

    • Wyck September 23, 2011 at 2:46 pm #

      Your approach is perfectly fine. It’s the approach I take as well.

      Years ago I saw a film called Happy Go Lucky, about a woman who seemed impervious to others’ moods because she was perpetually (and genuinely) perky. Yet she also read people accurately–too accurately I think. She tells her raving misanthrope of a driving instructor, “Were you picked on in school, Scott?” Later I found out from a psychology-major friend who watched the same film that she knew real people who were like the perky woman, and that they may be suffered from some sort of disorder (I forget what.)
      [Edited for clarity]

  2. Phoebe October 4, 2011 at 8:54 am #

    A couple of days ago, I met a 33 yr old guy. We happened to talk about school. He proudly told me that he was a black horse in the O levels. Scored badly for Prelims but very well for the Os. I carried on to ask him which JC he went to. He told me it was a long time ago and he cld not remember.

    I guess it is a touchy subject for him. But his answer was a disappointment to me. I rather he had said he doesn’t want to talk about it than give me such a dismissal reply.

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