22 Best Conversation Starters

Most of us don’t avoid conversations because we have nothing to say. We avoid them because we’re afraid of where they might go. 

We are biased, focusing on what can potentially go wrong in the interaction, forgetting what can go right. 

We often assume people won’t care, won’t listen, will judge us, or will react badly when we bring up something meaningful. So we avoid the conversation. 

But research suggests we’re usually too pessimistic. The other person often cares more than we expect, listens better than we predict, and the conversation is usually less awkward or explosive than we feared.

That’s what a good conversation starter really does. It’s not a party trick. It creates a low-risk opening for the kind of conversation that builds trust, deepens connection, and eventually becomes part of your legacy. 

 3 thoughts that help me start a conversation with someone I don’t know well 

Before I walk into a social environment, I don’t always feel completely confident. Sometimes I do. Sometimes I feel insecure. Most of the time, I’m somewhere in the middle.

This could be a Fourth of July party, church, a networking event, a business gathering, or any place where I know I’ll be around people I don’t know well.

When I start to overthink it, these are the thoughts I try to come back to:

1. Make a simple comment
Notice something around you and say something simple. It could be about the event, the setting, something that just happened, or something you genuinely appreciate.

2. Ask a curious question
Ask about something you notice, but avoid making it feel scripted or cliché. Genuine curiosity usually opens the door better than trying to sound impressive.

3. Don’t hesitate
Reach out and surrender the outcome. Don’t wait for the perfect opening or the perfect words. Sometimes the best conversations start a little awkwardly. Be willing to be a little sloppy and take the first step anyway.

Below are some of my favorite conversation starters organized by the kind of moment you’re walking into.

For a first conversation with someone new

1. What is something I would never realize about you unless you told me?
2. What’s something you’ve changed your mind about in the last year?
3. What’s something you’re genuinely excited about right now?
4. What’s something you’re curious about that most people wouldn’t guess?
5. If you had an unplanned free Saturday, what would you actually do with it? 

For family and people you already know well

1. What have been some of the happiest times in your life?
2. Is there something you’ve wanted to tell me but haven’t found the right moment for?
3. How do you believe you might be misunderstood?
4. What’s something I do that you wish I understood differently?
5. What do you hope people remember about you?

For close relationships, friendships, or even someone you’re dating

1. What’s something you need from me that you haven’t asked for directly?
2. When do you feel most understood by me?
3. Is there a conversation we’ve been circling instead of having?
4. What does it look like when you feel at peace, versus when you feel like everything’s fine on the surface?

For a conversation you’ve been avoiding, these are questions to ask yourself before actually having it

1. What’s the outcome you’re actually afraid of if you bring this up?
2. What would it cost you to stay quiet about this for another six months?
3. If this conversation went better than you expect, what would that look like?
4. What’s true that you haven’t said out loud yet? 

For crossing a divide, political, generational, or otherwise

1. What’s something you’ve experienced that shaped how you see this?
2. Where do we actually agree, even if we frame it differently?
3. What are you worried will happen if people like me don’t understand people like you?
4. What’s a story from your life that explains your perspective better than an argument would

How to actually use these

Don’t treat this as a script to read off. Pick one question. Ask it, then get quiet and actually listen to the answer before deciding what you think about it. The goal isn’t to perform curiosity, it’s to have it.

If you want a physical way to bring these kinds of questions into your home, the Legacy Jar was built for exactly this. It's a simple tool for prompting the conversations that matter most, with the people who matter most.

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