Conversation Starters

Hi there, if you want to communicate more authentically & improve your relationship with yourself and others, check out my YouTube channel.

It’s a good idea to keep a list of interesting conversation starters, for situations like the one below, where you want to skip the small talk…

You’re waiting for the bus. It’s running late. There’s a cute girl waiting next to you, just sitting there. “Should I talk to her?” — a voice in the back of your head.

Your shoulders tense up. Your breathing quickens. “But what would I say?”. Your heart’s pounding now.


“What do people usually talk about? The weather? The bus being late? But then what would I say after that small talk?! Ugh…” — 5 minutes pass.

“Oh crap, the bus is here. Do I sit next to her? No, that’d be weird because all the other seats are empty.”

Now you’re at the back of the bus and she’s at the front…

She gets off at the next stop and you never see her again.

Why You Should Prepare Conversation Starters In Advance

Strangers that spark our interest are a rare breed. You can’t go looking for them because they appear when you’re unprepared: in elevators, queues and cafes.

You want to talk to them, but you don’t. Because you can’t think of a good conversation starter that isn’t boring small talk.

(Also read How To Talk To People: The Simple Art of Meaningful Conversation.)

“It’s okay.” you tell yourself after you chicken out. I’ll start a conversation with the next interesting stranger I see. I’ll have something to say next time.

But you don’t. And it’s affecting your quality of life.

Start A Conversation

That girl in the bookstore might have taught you something new.

That guy in the cafe might have introduced you to your next client.

That girl on the bus might have changed your life in some other way… but you’ll never know.

You say you’re afraid of rejection, but it’s really not that easy to get rejected. You can say some pretty weird stuff to people and they’ll still be happy to talk to you.

For example… I’ve sat next to a girl in a park and sang the Pokémon theme song to her. She didn’t even know what Pokémon was but she gave me her number anyway.

I’ve stopped people in the street to talk about sex (see the video below).

I’ve walked up to two girls and said “I think I love your friend” to one of them. That was the beginning of a 3-year relationship.

People want to have fun, engaging and weird conversations, just like you do. They want to skip the small talk too.

But you’re afraid of saying the wrong thing or running out of things to say, right? And that’s okay.

That’s why I’ve included follow up questions with the list of thought-provoking conversation starters below. They’ll make it easier to keep the conversation going after you open it.

Your List Of Conversation Starters That Skip The Small Talk

So you’re back at the bus stop waiting next to the cute girl. You want to talk to her but you’re struggling to come up with something to say.

Here’s your line:

You: “Hey, can I ask you a weird question?”

“Ahh, okayyy, I guess.”

Then you pick your favourite conversation starter from the list below.

Level 1 Conversation Starters: Interesting Topics

  1. What’s something you don’t do enough? That you’d like to do more often.

    Follow up: What do you enjoy about that?

  2. What’s something you could just talk about for hours and never get sick of?

    Follow up: How did you get into that?

  3. What’s a good habit that you’ve put some effort into building?

    Follow up: Would you say it was worth it? Like how does it make your life better?

  4. When you were a kid, what did you want to be when you grew up?

    Follow up: Do you remember what made you want that?

  5. What aren’t you afraid of that some people are? First thing that comes to mind.

    Follow up: Why aren’t you afraid of it?

  6. What’s an unusual place you’ve travelled to?

    Follow up: Are you the kind of person who travels more for adventure or relaxation?

  7. What’s something you’ve done that everyone should try at least once?

    Follow up: So the people who haven’t done that… what are they missing?

  8. If I ask you to think of a book, what’s the first book that comes to your mind? … After Harry Potter.

    Follow up: Tell me about it.

Level 2 Conversation Starters: Personal Topics

  1. What’s something that annoys you? First thing that comes to mind.

    Follow up: Are you the kind of person who gets annoyed by little things or are you pretty zen?

  2. What’s something you’ve spent time wondering about lately?

    Follow up: Did you come to any life-changing realisations?

  3. Are you a risk taker, or do you prefer playing it safe?

    Follow up: Can you give me an example?

  4. What’s something your friends would say you’re good at?

    Follow up: What makes them say that?

  5. What’s something you tend to avoid doing? Even though you know you should do it.

    Follow up: What stops you from doing that?

  6. What’s the best advice someone’s given you? Or something you’ve learned?

    Follow up: Did you apply it?

  7. Are you usually lucky or unlucky?

    Follow up: What do you think makes you lucky (or unlucky)?

  8. Do you like change, or do you like things to stay as they are?

    Follow up: What’s the last big change you went through?

Important Tips That Will Help You Skip The Small Talk (Read These Before You Use The Questions)

Not every stranger will want to talk to you… but if they don’t, chances are you probably don’t want those people in your life either. The genuine connections you do make will be worth the rejections 100 times over.

Here are some additional tips to make people more open to skipping the small talk with you.

  1. Opening with “Can I ask you a weird question,” or something like that, shows that you understand that your question is out of the ordinary. It prevents them from thinking that YOU’RE weird… because you’ve acknowledged the weirdness.

    They’ll usually laugh, say something like, “Wow, that is a weird question…” and then happily skip the small talk with you.

  2. If they seem confused by your question, give them a reason why you’re asking. Like “Oh I just wanted to kill some time before the bus comes,” or “Oh I’m just curious… and I know I tend to skip small talk.”

    It doesn’t matter so much what the reason is. Just the fact that you’re giving them a reason when they’re confused shows that you have a certain level of social awareness, and that makes them more comfortable answering.

  3. If you find that people are saying “no” often, try changing the wording a bit so that the questions sound natural coming out of your mouth. Say it how you would say it.

    Try saying it in front of a mirror. Do you come across as genuine? Easy-going? Fun? Adjust your gestures, posture and smile until you do.

  4. If this is all still too difficult for you, then try starting at step one of these 10 steps that help you improve your conversation skills.

The more you skip the small talk with strangers, the less it’ll bother you when someone says no. You’ll stop taking it personally. You’ll become more confident genuinely connecting with people, and you’ll also become more comfortable with yourself.


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1 year ago