10 Fascinating Conversation Starters (or Meeting Icebreakers)

Before we get into 10 of my favorite conversation starters, we need to know:

What Makes a Bad Conversation Starter?

AVOID bad conversation starters at all costs. Bad conversation starters are:

Awkward: You know them; they are the conversations that make you feel itchy and have you wanting to run in the other direction. Avoid using these, unless you’re just being silly with your loved one.

Boring: These are the questions you fire off when you’re on autopilot… the questions you’ve heard over a HUNDRED times before… the questions that would even put the sheep to sleep. Social psychologist Mark Leary conducted a study on boring people, and the results were nothing short of harsh. People who were judged as being boring conversationalists were:

• liked less
• judged to be less friendly and enthusiastic
• harder to get to know
• judged less likely to be a strong or capable leader

Impersonal: These questions happen when you’re trying too hard to be polite. They show you’re not getting to know the other person on a deeper level (read: not showing enough character), so make sure to avoid impersonal questions—especially with your loved ones.

Offensive: Being offensive is one of the fastest ways to turn a close friend/loved one into your enemy or—even sneakier—a frenemy!  

Okay, so we know what to AVOID to have a great conversation! But…

What Makes a Good Conversation Starter?

A good conversation starter has the following traits:

Engaging: The conversation is new, exciting, funny, and it has emotion! The more you and the other person are emotionally invested in the conversation topic, the better the conversation!

Personal: Great conversation starters don’t just skim the surface—they dig deeper than the normal conversation would! Ask them something about their own life:

• their hopes, goals, and dreams
• the problems they’re currently facing
• how current events are affecting them

Open-ended: When you ask open-ended questions, you can easily follow up with other questions! Need help with open-ended questions? Here’s an example of how to rephrase:

• Not so open-ended conversation starter: “How are you today?”
• How to rephrase it: “What was the high point and low point of your day so far?

By asking open-ended questions, you’ll be able to follow-up with more meaningful ones, which happens to be the final quality of great conversation starters…

Meaningful: Great conversation starters have meaning. According to Harvard Researchers who analyzed over 300 conversations, they found that…

People who asked more meaningful follow-up questions were much more likeable!

So if your conversation starter has these elements, great! You’ve got one AMAZING conversation starter.

The 10 Best Starters for Great Conversation

Here are 10 conversation starters to try with your partner, kids and friends. They check ALL the positive boxes, and none of the bad ones.

Watch a video where I give a tutorial on all of these and why they work.

When can you try them?:

• with your partner over a long home-cooked meal
• when texting with friends you miss
• with your colleagues at the start of a video call
• with your kids as a break from TV

Here are my favorite conversation starters and meeting icebreakers to try right now!

1. What’s one thing you have always wanted to try, but never have? Why haven’t you done it yet?

I LOVE this question. It always surprises me. I also ask this question over and over again to the people I love because their answers change! You never know what you might discover about someone.

2. What has been the highlight of your year so far?

We need to focus on the positive. This question is a great way to get people thinking and reminiscing about what’s good.

3. What book, TV or movie character do you most relate to?

This is not an aspirational question—it’s not who you most want to be like. But rather, ask who you think you are currently most similar to. This can be fun because it often turns into a group discussion and everyone can help think of characters you are reminded of! It can be fun and dramatic.

4. What is your biggest regret?

Want to go deep? Then this question is for you! I find that this question can really bring you closer to the person you are speaking with. I am also always surprised at what I learn about people from their answers..

5. What do you daydream about?

Do you daydream about starting a business? Traveling the world? Calling that old crush? Now is the time to spill—and to hear people’s secret wanderings and desires. Or something silly. Some people daydream about the news, what they are having for dinner, or a movie they watched. The nice thing is that there are no wrong answers.

6. Who would play you in a movie?

Which celebrity do you look most like? I like this question because you can brainstorm together. It might even require some deep Googling. Bonus points if you can pick someone similar in age to you!

7. If you could trade places with anyone for one week, who would it be?

This is a really fun question because it requires you to think strategically. Some people pick fun and curious trades (think celebs and sports players), and others pick strategic ones (think political leaders and people from history). I’ll let you decide if people can switch with people both living and dead. Live on the edge!

8. What is something you have always wanted to learn?

New language? New skill? New idea? We have to encourage each other to keep learning, ESPECIALLY in times like these. This might kick off a great conversation about how you can start learning together.

9. What is your best memory?

I love a good story and this question is meant to get someone to share a good one. Whenever I ask this question I hear about amazing proposals, wedding days, and life highlights. 

10. What question have you always wanted to ask me? What do you wish you knew about me?

I love to end question sessions or deep conversations with this question. Usually someone has a secret knowledge wish—something they wish they knew about you. This is your opportunity to find out what.

Want more? Try my “36 Questions to Fall In Love”

…they are great for friends too! Researcher Arthur Aronson developed a set of 36 questions to fall in love. I actually used one above. Try all 36 with the people you care about.

You might also like:

• 3 Steps to Amazing Conversation: Our free mini-course on how to have deeper conversations.
• Our FREE Conversation Starter App
• 57 Killer Conversation Starters…in case you need even more conversation starters.

This article was originally posted on the Science of People blog.