50 Questions to Ask When You Don’t Know What to Say

Key Takeaways

• Questions are useful tools that help us understand people and their priorities.
• Forced social interactions don’t have to be awkward or exhausting. With the right questions, you can break the ice and have a lively discussion.
• Remember, the key is to be genuine, listen actively, and have fun.

We’ve all found ourselves stuck in those super awkward situations where conversation feels like a chore. Maybe we’re standing next to a coworker in the elevator, waiting in the buffet line with a distant cousin at a family wedding, or making small talk with a friend’s plus-one at a party. It’s not that we don’t want to connect—it’s just that it feels so…forced.

But don’t worry, we’ve got your back. Having a few go-to questions up your sleeve can help break the ice and make a forced social interaction less painful.

Event-Related Questions

These are some questions about the event or location that can help break the ice:

1. Have you been to an event like this before?
2. How do you know [the host]?
3. What brings you here today?
4. Have you tried the [food/drinks/activities] yet?
5. Isn’t this location amazing? What’s your favorite thing about the venue?
6. Did you come here with someone, or are you here by yourself?
7. Have you met anyone interesting here so far?
8. Are you from around here, or did you travel in for this?
9. Have you explored this area before? Any recommendations for what to check out nearby?
10. What’s been the most memorable moment for you today?

Personal Questions

These are some personal questions that can help you get to know the person better:

1. What’s your favorite way to relax and unwind?
2. What do your weekends look like?
3. Do you have any travel plans coming up?
4. Do you prefer to stay busy or take things slow?
5. What are you reading/watching at the moment?
6. What’s a song that’s been on repeat for you lately?
7. Do you believe in astrology? If so, what’s your sign?
8. What’s a guilty pleasure you’ll happily admit to?
9. What’s your biggest pet peeve?
10. What’s something you’re most grateful for today?

Work-Related Questions

These are some questions about work that can help you get to know the person professionally:

1. What do you do for work?
2. Which department do you work in?
3. What does your role involve?
4. What’s something about your job you really enjoy?
5. What’s your favorite part about working at [company]?
6. What’s the most interesting project you’ve worked on recently?
7. What’s the biggest challenge you’re dealing with right now?
8. What does work-life balance look like for you?
9. What was your dream job as a child?
10. What keeps you going when things get tough?

Family-Related Questions

These are some questions that can help you bond with the person over their family background and upbringing:

1. How’s [your partner/child/parent/relative] doing?
2. What’s one of your favorite memories with [shared relative]?
3. What’s your favorite thing about being a [parent/grandparent/uncle/aunt]?
4. What was it like growing up in [place]?
5. Do you get to see your family often?
6. What’s the funniest family story you can remember?
7. What’s your favorite family tradition?
8. What’s a phrase that’s used often in your family?
9. How do you usually spend the holidays?
10. What’s your favorite meal at home?

Hypothetical Questions

These are some lighthearted questions that can help you have a little fun together:

1. If you could have any job in the world, what would you pick?
2. If you could eat only one type of cuisine for the rest of your life, which one would it be?
3. If you could be anywhere in the world right now, where would you go?
4. If you could do anything in the world without worrying about time or money, what would you do?
5. If you could switch lives with someone, who would you change places with?
6. If you could have the birthday party of your dreams, what would it involve?
7. If you could cast a spell on the whole world, what would it be?
8. If you could have three wishes, what would you ask for?
9. If you could spend a day with anyone, alive or dead, who would you choose?
10. If you could go on a date with any celebrity, who would you like it to be?

Why Asking the Right Questions Matters

The right questions can transform a forced interaction into a meaningful conversation by creating opportunities for deeper engagement, says Tatiana Rivera Cruz, MSW, LCSW, a therapist at ADHDAdvisor.

But, how do you choose the right questions? “Think about what you’d enjoy talking about. What do you want people to ask you? Try to use those insights to figure out what the other person might like to talk about,” says Aimee Daramus, PsyD, a clinical psychologist at Clarity Clinic, Chicago.

Another helpful strategy is to ask open-ended questions, says Cruz, because they invite others to share their thoughts, experiences, and feelings in more detail. With luck, you may even be able to turn it into a fun conversation or a genuine connection.

By Sanjana Gupta

Sanjana is a health writer and editor. Her work spans various health-related topics, including mental health, fitness, nutrition, and wellness.

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