Here are 10 conversation starters you can use to stimulate a conversation with someone new:

1. How do you spend your free time?

2. What’s your favorite food?
3. Do you listen to any podcasts?
4. Have you heard of [movie or TV show you enjoy]?
5. What’s your favorite thing to do on the weekend?
6. Do you have any pets?
7. Do you have a favorite book?
8. What’s your favorite place to eat around [neighborhood]?
9. What would you choose if you had to choose one meal to eat for the rest of your life?
10. What’s your go-to karaoke song?

You don’t necessarily have to start a conversation with an icebreaker question. You can also
share a piece of advice you’ve recently learned from a book you’re reading, mention a funny
restaurant experience, or comment about something in your surroundings.

Remember: opening up the conversation is often the most challenging part. If you take the step
to initiate, you’ll likely make the other person feel more comfortable contributing. Should you
still feel nervous, use personal anecdotes to ease into the conversation and create jumping-off
points for the other person to share their point of view.

Getting to know you questions for anyone

It can be difficult to judge whether some questions are appropriate for your setting. For instance,
asking a manager who their celebrity crush is or about their exes is likely inappropriate in the
workplace.

If you’re speaking with a best friend, on the other hand, asking personal questions about the
craziest thing they’ve ever done and what their love languages are is often fine.

Here are some versatile questions to use whether you’re striking up a conversation with a
stranger or initiating a chat with a new colleague:

1. What’s your latest guilty pleasure?

2. What was your favorite subject in school?
3. If you could choose a superpower, what would you pick?
4. What’s your favorite holiday?
5. When was the last time you went to a concert?
6. What was your least favorite food as a kid?
7. Do you have a favorite sport?
8. What’s the funniest joke you’ve ever heard?
9. What’s your biggest fear?
10. What was your first job?

Personal questions to ask people

Once you become comfortable with your conversation partner, you may want to dive into more
personal questions to strengthen the bond.

If you’re in a laid-back, casual setting, this could be as simple as posing funny would you rather
questions. If you’re in a more intimate, you may want to ask interesting questions to get to know
the other person on a deeper level.

Here are some of the best questions to get to know others personally:

1. Is there anything you dislike in your work life?

2. Do you have any pet peeves?
3. What was your dream job as a child?
4. If you could have dinner with anyone, who’s one person you’d go with?
5. Do you have a favorite childhood memory?
6. What’s the last thing that made you cry?
7. What’s your favorite season, and what does it remind you of?
8. What does a perfect day look like?
9. Do you have any hobbies?
10. If you could only listen to one song for the rest of your life, what would it be?

Fun questions to ask people

Whether you’re at a work party, community event, or meeting in-laws for the first time, asking
light-hearted questions is a great way to get to know the unique personalities around you. Fun
questions can make others laugh, loosen up tension, and make connecting easier.

Here are several go-to questions to ease nerves and make a positive first impression:

1. What’s your favorite midnight snack?

2. Who would you choose if you could be friends with a fictional character?
3. What’s the best costume you’ve ever worn to a party?
4. What’s the best surprise you’ve ever received?
5. What’s the most embarrassing moment you’ve ever experienced?
6. If you could have any talent, what would you choose?
7. If you were stuck on a deserted island and had to choose a family member to be stuck
with, who would you choose?
8. Who would you be if you had to be a character from a book?
9. What’s your funniest relationship dealbreaker?
10. If you had to live in a fiction movie, which would you choose?

Deep questions to get to know someone

It’s normal to feel hesitant about diving into deep discussions. However, it can be a fast way to
build connections through shared experiences and understanding. You may even find comfort in
learning that a previous subject you felt alone in is relatable to someone around you.
It can feel vulnerable to share personal information, so when you do so, it shows the other person
that you trust them. Remember: if you’re having a serious discussion with someone, always
remember to listen actively and make their feelings feel valid.

Here are some examples of deep questions you can ask to build close connections and trust:

1. Do you ever feel lonely?

2. Is there anything you’re afraid you won’t accomplish?
3. What’s your biggest fear?
4. Is how you define success different today than it was when you were younger?
5. What’s the most meaningful relationship you’ve ever had?
6. Do you have any toxic traits you’re not proud of?
7. What are some difficult lessons you’ve learned from past relationships?
8. What’s number one on your bucket list?
9. What’s your favorite memory?
10. What would you like people to remember you for?

Questions to ask people at work

It’s essential to read the room when asking questions, as each person will have a different
perspective on what’s appropriate. The questions you’d ask on a first date aren’t necessarily the
same ones you’d ask your boss. If you’re unsure of what’s acceptable, you can always stick to
work-related topics to avoid any unwanted awkwardness.

Here are some work-friendly questions you can ask your colleagues or higher-ups:

1. What’s your favorite part of your job?

2. What was your first job?
3. Do you have any side hustles or projects?
4. When you work remotely, do you work in a cafe or from home?
5. What’s something valuable you’ve learned during your career?
6. Are there any upcoming projects you’re excited about?
7. Did you ever think about trying a different career before this one?
8. What made you want to work for [company]?
9. Did you go to school to become a [job role]?
10. Do you have any tips for time management?

How to get good at asking people questions

Asking good questions is a learned skill, and even the most social extroverts can benefit from
brushing up on their talents. Here are some valuable tips to keep in mind for your next
conversation:

Be curious
Staying curious opens you up to a world of knowledge and valuable insight. You’ll learn more
about yourself and the people around you through the stories, ideas, and perspectives they share.
And if you never ask questions, you’ll never know what life experiences they hold.

A hint of curiosity will help you navigate through the conversation naturally and ask follow-up
questions. And in doing so, your conversation partner will also perceive you as engaged,
receptive, and thoughtful.

Here are a few examples of intriguing follow-up questions:

1. What exactly do you mean when you say [idea]?

2. Why do you think [situation] upset you?
3. How did you learn about [concept]?
4. Can you give me an example?
5. Can you tell me more about that experience?
6. How did you arrive at that conclusion?

Avoid rapid-fire questions

No conversation should feel like an interrogation. A good talk flows naturally and has equal give
and take. Remember: your questions are the conversation starter, not the entire show.

Ask a couple of questions to build familiarity, find common ground, and let the chatter carve its
own path. Don’t be afraid of silence — sometimes, pausing provides an excellent opportunity to
reflect on what’s been said.

Practice active listening

Active listening involves paying close attention to what the other person is saying and listening
to understand rather than to respond. Use eye contact to show interest, and remember to give
your full attention to your conversation partner.

Keep in mind that a lot of human communication goes unspoken, so you may want to practice
using body language to show others you’re listening and engaged.

Work on your confidence

Building confidence can help you become less hesitant about asking questions.

When you’re secure in your communication skills and valuable traits, you’ll be less worried
about how others perceive you. You can build these skills by asking more questions or attending
events that place you outside of your comfort zone.

Here are some valuable tips for boosting your confidence:

 1. Stop comparing yourself to others: Avoid focusing on those around you. Maybe your
friend is naturally charismatic, or a colleague always asks the right questions to make
people laugh. Everyone has different skills — including you.
2. Prepare questions: If you’re anxious about an upcoming meeting or date, brainstorm
questions beforehand. You can write them down on your phone, think of possible
answers and follow-up questions, or even practice with a trusted friend.
3. Practice positive self-talk: It’s easy to be unnecessarily hard on yourself or strive for
perfection. Remember to look back on your progress with pride and celebrate your wins,
no matter how big or small. Remind yourself of your value, and don’t forget that there’s
only one you, and that’s an asset.

What to avoid when asking questions

Knowing what not to say can save a conversation from running dry. Here are a few things to
avoid to foster a good discussion:

1. Avoid “Yes” or “No” questions: Closed-ended questions are a fast way to shut down a
conversation. When you ask too many queries that require one-word responses, your
conversation partner can’t offer a detailed answer. Instead, ask open-ended questions to
allow others to reflect and provide more meaningful responses.
2. Be careful when discussing personal beliefs: Not everyone has the same beliefs, and
that’s okay. Sometimes, discussing political or religious values can quickly become
heated, even with people you consider friends. If you’re unsure about a topic, you should
ask if they’re comfortable discussing it before posing any questions.
3. Don’t only ask questions: Don’t be afraid to share your thoughts and ideas when others
ask about you. A conversation is also a way for new people to learn more about you.
When you don’t share information, the other person may feel you don’t reciprocate their
want for connection.

Getting the conversation started with questions

You can learn hundreds of questions to ask to get to know someone, but you still need to have
the courage to ask them. Fortunately, practice makes perfect. The more questions you ask, the
better your conversation skills will be.

A deep conversation builds trust and shows others that you care about their perspective and
ideas. Remember to read the room, listen attentively, and ask follow-up questions to keep the
ball rolling.