Tag Archives: conversation

It all goes downhill after this

24 Nov

Whenever I greet a new stranger at the lobby of my apartment, they seldom ask me, “Did you just move in?” Or even a more basic, “Do you live here?” What they ask is, “Are you a tenant?” and, “How much do you pay for rental/the house?”


People in Singapore have a bad, bad habit of asking new acquaintances about their jobs, salaries, education, etc.

Most cultures don’t do this. When I travel overseas, or when I entertain foreign visitors, we talk about hobbies, friends, passions, current affairs, our respective awful climates. I don’t get asked (nor do I ask) questions like, “What company do you work at?” The closest I get to that is, “What do you do?”

I’m not saying this to bash local culture. I’m saying this because it’s an important boundary to respect when meeting new people.

Have you ever asked someone about their job, only to have them give a generic answer, like “Executive”? Have you ever asked been about where you study, only to have to answer, “Oh, just some neighbourhood school. You’ve probably never heard of it.” Did the conversation stop dead, right there?

Or did you ask, “Well… what, exactly?” and get a curt, “I don’t think I know you that well?”

Asking strangers and new acquaintances about their jobs, or salaries–or anything to which people attach social status–is bad because it’s often a direct assault on their egos.

Let’s reverse the roles, and suppose a date asks you what you do for a living. If you answer, “I’m a doctor,” she might think,  “Wow, someone’s boasting here.” Or she might think, “Does this mean I’m not good enough for this person’s company? What if he asks me what I’m doing?” Or, “Uh-oh, it sounds like he’s got a more interesting job than me… what do I say next?” If you answer the question directly, you can’t predict her reaction. If you avoid the question, she’d think you have something to hide.

If you’re at the receiving end of such an insensitive and ill-judged question, there’s really very few things you can do to keep the conversation from going downhill. To me, it’s not your responsibility to keep a conversation from turning awkward once the other’s party’s started down that part.

But you shouldn’t do it yourself.



How to talk to women (when they are busy running)

22 Sep

WordPress’s Freshly Pressed page recently featured a funny, well-illustrated article on how to greet fellow runners when you’re out jogging. I thought it was a funny way to frame the subject of how to talk to strangers, something that so many dating gurus seem to be obsessed with.

There’s so much advice out there on how to talk to a woman when her attention is obviously elsewhere–something which I feel is the exact opposite of being socially aware.

Saying Hi to women is not a hard thing to do–provided that’s all you’re trying to do. If you think it’s hard to think of chat-up lines when you’re running, imagine how hard it is for a woman to feel flattered she’s running!

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.

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Don’t talk to yourself while you’re talking to a woman

30 Dec

While dating involves both the man and the woman, women’s and men’s perspectives are usually quite different. While it’s useful to get a woman’s take on dating issues, their advice shouldn’t be taken at face value.

Take this article for example: “How can I tell men I just want to be friends and not date them?” (Read it first before you continue.)

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The ‘things’ person vs. the ‘people’ person

13 Dec

What do the braggart, the enthusiast, and the bore have in common?

One: They are top on the list of dates that women dread.

Two: They’re what I call ‘things’ people—people who are interested in things, not people.

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