How to get a conversation going

sazuna45 asks: There is this guy I like. He’s kind of a friend and he is super friendly whenever he’s alone and I’m alone. So I want to talk to him but I really don’t know how to start a conversation. Please advise me! I can’t just say ‘hi’ cause then he’ll answer and walk away. Something that’ll keep a conversation longer?

Hi sazuna45 –



Your problem is a really common one.  You want to get a conversation going, but nothing you say gets that effect.  It’s like when I’m at the dog park, and I try to get the boy dogs to chase me, and they’ll notice me and run after me, but just for a second, and then walk over to something else.  How irritating!


The main trick I know for conversation is something called “Open-Ended Questions.”  For example, let’s say you want to ask this boy about his day at school.  If you say, “How was school today,” he might answer “Fine.”  If you ask, “Do you like the new math teacher,” he might say “yeah.”  And you’re nowhere.

But if you ask “What do you think of that new math teacher?  I heard he’s a big improvement over the last one,” it’s going to take him a bit more effort.  He might say “Oh he’s all right,” but you can follow that up with “So you mean you like him better than the last one?  Why?”

What you really want to get to is questions that start with “Why” or “How,” because those require him to open up.  “When was the Boer War” can be answered with a four-digit number. “How was the Boer War fought” requires a lot more words. And “Why was the Boer War fought” requires a lot more!


So, now that you know what sort of questions to ask, the question is what you want to ask about.  And for that, look to him.  What are his interests?  What’s he excited about?  What does he just hate?  Those are all great topics for getting conversations going.  And if you don’t know some of the things he’s interested in… conversation is a great way of finding that out.  “Hey student elections are coming up in a week.  Do you have an opinion about who should be elected?”  If he says no, then fine.  But when you ask him about something and he says yes, he’s interested, you’re in!


Just imagine you were trying to start a conversation with me.  Now you might ask “Shirelle, did you get to chew on a bone last night?” And I might say “Why, yes I did, thanks for asking.”  Conversation is Over.  But if you ask me “Shirelle, how was that bone you had last night?”  Oh, then I might talk for an hour about it!


So try those things out – “How,” “Why,” and subjects that really affect him.  Between those, I think you’ve got a great chance.


Have fun!




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