It can feel awkward when the chat starts to fade and you’re not sure what to say next, but with the right questions, you can keep any conversation flowing smoothly and make deeper connections with people. This article will give you lots of go-to questions for different situations. You’ll find ideas for chats with new people, friends, coworkers, and more!

Open-Ended Versus Closed Questions

Open-ended questions invite longer, more detailed answers. They start with words like “how,” “why,” or “what.” Closed questions usually get a short, specific answer like “yes” or “no.”

Examples of open-ended questions:

• What’s your favorite childhood memory?
• How did you get into your current job?
• What’s the most exciting trip you’ve ever taken?
• Why did you choose to live in this city?

Examples of closed questions:

• Do you like travelling?
• Have you ever been to Europe?
• Are you a morning person?

Open-ended questions are often better for keeping the conversation going.

Questions to Ask to Keep a Conversation Going: Examples for Different Occasions

Asking the right questions can make your conversations more engaging and meaningful! Below you will find examples of great questions to help you keep the talk flowing in various settings.

Questions to Ask at Networking Events

• What brought you to this event?
• What do you enjoy most about your work?
• What’s the biggest challenge in your industry right now?
• How did you get started in your field?
• What’s the most exciting project you’re working on?
• What’s your favorite part of networking events?
• What’s your go-to app for productivity and why?
• How do you stay updated with industry trends?
• What’s the best career advice you’ve ever received?
• What’s your dream job?
• What’s the most interesting place your work has taken you?
• How has your industry changed since you started?
• What skills do you think are most important in your field?
• If you could learn any new skill, what would it be and why?

Questions to Ask At Social Gatherings

• What’s your favorite local restaurant?
• What’s the best vacation you’ve ever been on?
• What’s your favorite way to relax after a long day?
• If you could travel anywhere right now, where would you go?
• What’s the best concert you’ve ever been to?
• Do you play any sports or exercise regularly?
• What’s your favorite season and why?
• What was your first job?
• Do you have any hidden talents?
• What’s the most adventurous thing you’ve ever done?
• If you could have dinner with any celebrity, who would it be?
• What’s your favorite childhood memory?
• If you could instantly become an expert in something, what would it be and why?

Questions to Ask in a Workplace

• What project are you most excited about right now?
• How did you end up in your current role?
• What’s your favorite part of working here?
• What’s the most interesting thing you’ve learned at work lately?
• How do you like to celebrate your wins at work?
• What’s your ideal work environment?
• If you could switch jobs with anyone in the company for a day, who would it be?
• What’s the best career advice you’ve ever gotten?
• How do you stay motivated during busy periods?
• What’s your go-to lunch spot near the office?
• What’s the most challenging part of your job?
• How do you unwind after a stressful day at work?
• If you could add any perk to our workplace, what would it be?
• What’s your favorite way to collaborate with the team?
• What’s the most valuable skill you’ve gained in this job?
• If you could create a new position at the company, what would it be?
• What’s your proudest work achievement so far?

Deep Questions To Keep the Conversation Going

Deep questions help build stronger connections by exploring thoughts, feelings, and experiences. They often touch on personal topics and values:

• What’s the most important lesson you’ve learned in life?
• Who has had the biggest influence on you?
• What’s your biggest fear?
• What makes you feel truly alive?
• If you could change one thing about yourself, what would it be?
• What’s your definition of success?
• How do you want to be remembered?
• What’s the hardest decision you’ve ever had to make?
• What’s your biggest regret?
• What’s the best advice you’ve ever received?

Fun Questions to Ask to Keep the Conversation Going

Fun questions keep conversations light and enjoyable. They’re great for breaking the ice or adding some humor to a chat:

• If you were a superhero, what would your power be?
• What’s the weirdest food you’ve ever tried?
• If you could have dinner with any celebrity, who would it be?
• What’s your go-to karaoke song?
• If you could instantly become an expert in one thing, what would it be?
• What’s the most embarrassing thing that’s happened to you?
• If you could travel back in time, which era would you visit?
• What’s the strangest dream you’ve ever had?
• If you were a flavor of ice cream, what would you be?
• What’s the most useless talent you have?

Questions About Leisure and Entertainment

• What’s the last great movie you watched?
• Do you have any favorite TV shows you’re watching right now?
• What kind of music do you enjoy?
• What’s your go-to activity for relaxing after a long day?
• Do you have any fun weekend plans coming up?
• What’s your favorite way to spend a day off?
• Have you picked up any new hobbies recently?
• What’s the best book you’ve read this year?
• Do you like to cook? What’s your specialty?
• What’s your favorite restaurant in town?
• Which teams do you follow?
• What’s the most fun vacation you’ve ever taken?
• Do you have any travel plans for the future?
• What’s your favorite outdoor activity?
• What’s your ideal way to spend a rainy day?
• What’s the best live performance you’ve ever seen?

Questions About Personal and Professional Achievements

• What’s the biggest challenge you’ve overcome recently?
• How did you celebrate your last big win at work?
• What skill are you trying to improve right now?
• Can you tell me about a project you’re really proud of?
• What’s the best piece of career advice you’ve ever gotten?
• How do you balance your work and personal life?
• What’s your dream job?
• How did you choose your current career path?
• What’s the most valuable lesson you’ve learned at work?
• What’s the biggest risk you’ve taken professionally?
• How do you stay motivated at work?
• What’s your strategy for handling workplace stress?
• Have you ever changed careers? What was that like?
• What’s your biggest professional goal for the next year?
• How do you measure success in your job?

Questions About Cultural and Current Events

• Have you been following the developments in [current event]?
• What do you think about [recent cultural trend]?
• What’s your favorite news source?
• How do you think technology is changing our society?
• What’s your opinion on social media’s impact on culture?
• What do you think are the biggest challenges facing our generation?
• How do you think [recent event] will affect the future?
• What’s your favorite way to learn about different cultures?
• What’s the most surprising thing you’ve learned about another culture?
• How do you think our city/country has changed in the last few years?
• What’s your favorite holiday tradition from your culture?
• Have you ever lived in a different country? What was that like?
• What’s the most interesting museum you’ve visited?
• If you could solve one global problem, what would it be?

Handling Awkward Silences

Awkward silences can make you feel uncomfortable, but they don’t have to end the conversation. Try these strategies to break the ice:

1. Ask about their hobbies: “What do you like to do for fun?”
2. Bring up current events: “Did you hear about the new movie coming out?”
3. Share a funny story: “The funniest thing happened to me today…”
4. Ask for their opinion: “What do you think about [topic]?”
5. Compliment something about them: “I love your shoes! Where did you get them?”
6. Talk about food: “Have you tried any good restaurants lately?”
7. Discuss travel: “If you could go anywhere, where would you visit?”
8. Ask about their job: “What’s the best part of your work?”
9. Bring up mutual friends: “How do you know [friend’s name]?”
10. Talk about plans: “Do you have any exciting weekend plans?”

A little silence is okay. It gives you both time to think.

Dealing With Difficult Topics

Sometimes conversations can turn to sensitive subjects:

1. Show empathy: “That must be really tough for you.”
2. Acknowledge their feelings: “I can see why you’d feel that way.”
3. Ask if they want to talk about it: “Do you want to discuss this more?”
4. Offer support: “Is there anything I can do to help?”
5. Take a break: “Would you like to take a moment before we continue?”
6. End the topic respectfully: “I appreciate you sharing that with me.”
7. Change the subject gently: “On a lighter note, [any open-ended question]?”