The Small Talk Chronicles: Good Questions

Part one in this series.

One of the most difficult things about small talk (at least for me) is figuring out what sort of questions are both appropriate and interesting for the setting.

Inquiries like where do you work?, are you married? or do you have kids? seem to be fairly common. There’s absolutely nothing impolite about asking any of these, of course.

The issues I have with these questions are as follows:

  • They’re a little boring.
  • They can easily lead to conversational dead-ends if someone doesn’t have a job or family or isn’t happy with what they do have.
  • If you don’t have the “correct” answer some people will proceed to tell you exactly what you’re doing wrong with your life. :O

This isn’t to say I never ask these types of questions, only that it’s good to have a back-up plan.

So far I’ve learned that I prefer open-ended questions that can be scaled to include more or less personal information and that I already know how I’d answer.

For example I love asking, “what do you like to do?”

Everyone has something in his or her life that brings a spark to his or her eye. When you figure out what that something is – often even if it isn’t necessarily something you’re knowledgable of – it breathes new life into the conversation.

It’s such an open-ended question that someone who loves her job could mention that while someone else who is passionate about his kids, her hobby, his volunteer work, her spiritual awakening would be free to talk about those aspects of their lives as well.

This is also a highly scalable question. By that I mean that it can be adapted to fit any situation – work parties, family gatherings, wedding receptions, or job interviews. How much the person who answers this question decides to reveal can expand or contract as well.

 How did you meet our host?

Or, alternatively, how did you decide to volunteer or work with this organization?

I like this question because it so easily leads to stories. Was your new acquaintance once set up on a hilariously doomed blind date with the host? Did he or she first become interested in the organization because relatives worked there? There are so many possibilities.

Are you planning to attend event X?

One of my favourite things about living in Toronto is that there’s always something free to check out on the weekends, from festivals to parades, rib fests to art fairs.

Not everyone plans to check out events like The Pride Parade, Buskerfest, or the Toronto Jazz Festival, of course, but enough do that it’s worth it to ask if there’s a particularly well-attended event coming up in the near future.


What are your favourite questions to ask when you don’t know someone well?

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0 Responses to The Small Talk Chronicles: Good Questions

  1. Your questions are great!  And personally I hate being on the receiving end of the “usual” questions you mention because I don’t have standard answers to any of them and my answers just lead to people telling me what I’m doing wrong.  Your questions allow anyone to answer in ways that fit them.  I don’t have any questions to add to your list (I don’t go out much) but I’m sure going to try to remember yours when I am caught in such situations!

  2. I’ve always feel awkward making small talk, because I loathe those canned questions.  So I tried branching out with the question “Where do you like to go on vacation?”  I’ve found that it is a little tricky, because you could be talking to someone who is under too much financial constraint to take vacations, or someone whose idea of vacation is just sitting at home.  However, you can learn a lot about someone when it does work.

    It’s also not as flexible as “What do you like to do?”  I think I like that a little better.  Great question!

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