How To Start Conversations With Fun Questions

No idea what to say? No problem.

Three men at a social gathering enjoying a conversation.

As we get older, our chances of experiencing social isolation — a lack of social connections that leave you feeling lonely — go up. Maybe we’re living alone because our loved ones are gone or have moved away. Perhaps a chronic illness or hearing loss makes us reluctant to leave the house.

If any of these situations sound like you, you may have forgotten how to interact with others in social settings or find the mental effort of having a conversation a bit exhausting. Because research shows social connections are good for your health, we’re sharing some icebreakers you can use to keep conversations flowing, whether you’ve just met or known them for a long time.

Finding some common ground for a discussion can help you plant the seeds of connection that lead to less loneliness in your life. Learn how to start or continue a conversation with these questions designed to “break the ice” and encourage relationships to blossom.

Tried-and-True Icebreakers

Start an interesting conversation

Getting into the swing of socializing is easier when you have a few icebreakers in your back pocket. After you’ve introduced yourself, ask a question that helps you find a subject to talk about.

What’s the best piece of advice you’ve ever been given?
When you die, what do you want to be remembered for?
What is your favorite item you’ve bought this year?
What is your absolute dream job?
Have you ever been told you look like someone famous — who was it?
You have to sing karaoke, what song do you pick?
Who was your childhood actor/actress crush?

Ask “getting to know you” questions

After you’ve introduced yourself (or been introduced by someone else) at an event, repeat the other person’s name right away to help you remember it. “It’s a pleasure to meet you, Joe. So tell me…” and ask one of the questions below:

Where did you grow up?
If you could be anywhere in the world right now, where would you be?
What was the first album you ever bought?
Are you a beach or mountains type of person?
What is your favorite food or type of cuisine?

Making eye contact, paraphrasing what’s being said, and avoiding the urge to interrupt are just a few of the active listening skills you can use to begin to build a connection.

Use fun questions to deepen connections

Icebreakers don’t just get conversations moving; they also help build a shared sense of belonging. At your next volunteer or co-worker meeting, go around the room and ask each person to answer one of the following questions.

What three items would you bring with you if you were going to be stranded on a desert island and why?
If you could have any superpower what would it be and why?
What famous person do people say you look like?
If you could have any celebrity over for dinner, who would it be and why?
What song best describes your life right now?
If you have regular meetings with a volunteer, interest, or work group, kick off each week with a different question to keep the conversations flowing.

What to Say if Tensions Flare?

Tricky topics may come up. But that doesn’t mean you have to avoid a conversation that may touch on potentially sensitive issues that reveal you have different political views.

If a discussion gets heated — someone has strong feelings against gun control measures — you can lessen the emotional charge by validating how they are feeling, rather than how they are behaving.

Say “I know what you mean — these times are scary.”

It may also help to clarify what the person means by reflecting back to them what they’ve said.

“It sounds like you’re needing some ways to protect yourself and feel more in control. Is that right?”

Finally, you can always change the subject by asking a question on another topic. A good question to always have in your back pocket: “Tell me, what do you like to do in your spare time? I’m always interested in learning more about people’s hobbies.”

Icebreaker Games

Play a game of “would you rather”

“Would You Rather” works with people you’ve just met as well as with people you’ve known for a while. To play, take turns going around the room and ask each person one of these questions:

Would you rather only have summer or winter for the rest of your life?
Would you rather go on a hike or see a movie?
What is your favorite item you’ve bought this year?
Would you rather never use social media sites and apps again, or never watch another movie or TV show?
Would you rather give up sweets or salty snacks?
Would you rather spend a week in the forest or a night in a real haunted house?

Share two truths and a lie

This classic game is another fun way to get to know friends, family, or people you just met on a deeper level. To play, each person takes a turn sharing three statements about themselves: two of the statements are true and one is false. Next, the other players try to guess which is the lie by asking questions.Here’s an example:

“I’m from Boston, I’m allergic to shellfish, and I love Brussels sprouts.”

The lie was “I’m allergic to shellfish.”

Host trivia over video chat

If you’re looking for a remote icebreaker game, playing a trivia game is a fun way to build connections. Sign up for a free account on Kahoot or Quizwitz to play a variety of trivia games.To run this remotely, you’ll want to share your screen with your team. Everyone will need to have a separate device to use so they can enter the game and submit their answers.

To host virtual trivia, try one of these free video apps:

Facebook’s Messenger Rooms
Google Meet
Skype Meet Now
Zoom
WhatsApp

Of course, any of the icebreaker questions or games mentioned above also work over video. So if you have a regular virtual meetup or chat with family, switch things up each time by rotating your icebreaker.