150+ Funny Conversation Starters To Connect At Workplace

Christina J Colclough

By Christina Colclough

Last updated:

Funny Conversation Starters

Let’s face it: it’s sometimes an uphill battle to stay relevant in a diverse company culture. There is no shortage of moments where everyone freezes, and you just can’t utter a single word. Here comes your lifesaver: some interesting openers to break the ice! Scroll down to check out my inclusive list of funny ways to start a conversation!

30 Simple, Good Conversation Starters

These classic openers can be applied in almost any situation. They are also quite easy and anything but intrusive, encouraging more comfortable responses.

1. What is your favorite pastime/hobby?

2. What is your comfort food or favorite drink?

3. What book have you read recently?

4. When is your last vacation? Is there any travel coming up?

5. Are you an early bird or a night owl?

6. Any plans for this weekend?

7. Do you have any silly nicknames?

8. If a food can describe your personality, what would it be?

9. What is your favorite restaurant now?

10. Do you believe in ghosts/aliens?

11. What is currently topping your bucket list?

12. Have you ever attended any concerts before? What was the first one?

13. What is the funniest joke/ stupidest joke that never fails to make you laugh?

14. What is the worst/best thing you’ve bought?

15. If you could have a magical power, what would it be?

16. What was the last thing you searched on Google?

17. What’s the craziest Wifi name/password you’ve seen?

18. What is a favorite memory from childhood that you often think about?

19. Have you ever come across any famous person?

20. What movie/TV show have you been watching recently?

21. Do you have any pets? Do you love dogs or cats more?

22. What is your guilty pleasure?

23. What is your most annoying pet peeve?

24. What is the best/worst gift you’ve ever got?

25. What is your favorite song for karaoke?

26. What is the weirdest or craziest food you’ve ever tried?

27. What is your favorite Disney or fictional character?

28. Do you have any crazy life hacks?

29. Do you often listen to podcasts? Any recommendations for me?

30. The new Star Wars movie, [Movie Title], is finally here! Are you excited to see it?

20 Funny Topics To Talk About At Work

manager joking with his junior colleagues

A little humor can go a long way, loosening the tension and awkwardness without appearing unprofessional at the workplace. Try cracking a joke or initiating a meaningful conversation on some funny yet not-too-personal topics like the ones below:

1. What is the weirdest thing you’ve done in others’ houses?

2. What horror movie scared you as a kid and still creeps you out today?

3. What’s the most unexpected thing a coworker has ever done?

4. What’s the silliest thing you’ve ever done in our company’s elevator?

5. How would you react if someone pranked you at the office?

6. Just for fun, how would you lighten the mood around the office with a harmless prank?

7. Do you have any plans to escape this meeting and become professional beach bums?

8. What’s the craziest excuse you’ve heard someone use to get out of work?

9. Have you ever accidentally sent an email meant for your friend to your boss?

10. What is your funniest oops story at work?

11. Would you rather have an office that’s freezing all the time or one that’s constantly sweltering?

12. That’s enough stress for June. I’m ready to welcome July. Who’s with me?

13. What is the funniest/craziest tidbit you’ve heard from the grapevine at the office?

14. Did anyone see a ghost in the breakroom this lunch? Or was that just me hallucinating from lack of coffee?

15. My brain is officially on vacation mode now. Who’s with me at the beach?

16. Your outfit kills it today! Did you come back from a fashion show or something? 

17. What’s the oddest food you’ve ever eaten at your desk?

18. What’s the most ridiculous thing you’ve ever had to explain to a colleague?

19. If you could swap jobs with anyone in the company for a day, who would it be and why?

20. What is the silliest presentation you’ve ever made at work?

15 Unique Conversation Topics At Workplace

It’s time to get out of the box! Put in a bit of your imagination, and you’ll come up with some one-of-a-kind topics that get a few laughs bouncing around the office. Note that these conversation starters might not resonate with someone you’ve just met for the first time.

1. If you could visit any era in history, which one would you choose and why?

2. If money wasn’t an issue, what would be your dream job?

3. If you had to create your own reality show, what crazy competition would it be?

4. What would you wish for if a genie granted you three wishes?

5. If you had 24 hours where you couldn’t be hurt, what daring things would you do?

6. If you had the chance to move to Mars, what would be the first thing you’d do there?

7. If you could gather five celebs for a dinner party, who would you invite, and what would you talk about?

8. Did you ever have a pretend friend when you were a kid?

9. If you could switch lives with anyone for a day, who would it be, and what would you hope to learn from their perspective?

10. What would you do with the money if you won a giant lottery jackpot?

11. If you could attempt any world record, even if it’s a bit silly, what would you want it to be for?

12. If your pet could speak, what embarrassing or funny stories might they tell?

13. Do you have a knack for something that seems useless?

14. If a movie about your life were made, what genre would it be, and which actor would you choose to portray you?

15. Imagine you have an extra 60 minutes each day. How would you use it?

20 Clever Conversation Starters To Connect With Team Members

Team Building Activities For Problem-Solving

Building rapport with your colleagues keeps everyone connected and boosts team productivity. If you feel like the relationship with your coworkers has hit a wall, it’s time to rekindle the connection with some engaging, fun conversations.

1. Have you been working on any new projects recently? How’s it going?

2. Are you swamped right now/Have you been busy recently?

3. How long have you worked in this company?

4. What is the most unexpected side gig or job you’ve ever had?

5. Where do you like to take a nap/rest at the office?

6. What team-building activity do you like the most at work?

7. What’s the weirdest thing a hiring manager has ever asked you in a job interview?

8. What pick-me-up do you like at work? Coffee, tea, or snacks?

9. We’ve been swamped recently. What do you often do to unwind after work?

10. Do you describe yourself as an extrovert or an introvert?

11. After everything we’ve been through, don’t you think we all deserve a vacation?

12. Hey, I know things have been tough with [their problem]. Is there anything I can do to support you?

13. I sense a lot of tension from you lately. Would you like to talk about it?

14. These long workdays have been exhausting. How are you managing?

15. Hey, I’ve been concerned about you. Are you doing okay?

16. What’s one skill you’d love to learn?

17. What’s one nice thing a coworker has done for you?

18. What’s your favorite part about working on our team?

19. Is there anything you’ve learned recently that you’d like to share with the team?

20. What are you hoping to achieve in your career in the next few years?

30+ Deep Questions To Start A Conversation

The line between showing you care and invading someone’s privacy is just one question away. So, be mindful when choosing conversation starters and consider who you’re talking to. Are they close enough to be comfortable sharing personal matters? If not, start with a general, simple question instead.

1. Have you ever experienced a really unusual coincidence?

2. What is the best or worst advice you’ve ever got, and how did it impact you?

3. Has anyone given you some unsolicited advice that was really helpful?

4. Are there any phrases or words that drive you nuts?

5. Do you have any goals you’re currently pursuing outside of work?

6. What’s the most memorable place you’ve ever visited? Do you plan on going back?

7. Have you ever been seriously injured? What happened?

8. Can you share an experience that helped you realize your limitations?

9. If there was one thing you could do for your whole life, what would it be?

10. What’s your typical morning look like?

11. Is there a situation you hope you never have to deal with again?

12. Do you have a treasured possession?

13. What’s the strangest talent that makes you stand out?

14. Does your name have any special meaning?

15. What’s the most awkward thing that’s ever happened to you?

16. What’s one thing you own that you wish you didn’t?

17. Which celebrities do you follow closely on social media?

18. What’s one thing you’ve never told your best friend but will share with me?

19. Where do you see yourself in 10 years?

20. How do you define success?

21. What’s your personal motto?

22. What piece of advice would you give your 18-year-old self?

23. Is there a lesson you had to learn the hard way?

24. What’s your proudest accomplishment?

25. Do you have any regrets?

26. When are you the happiest?

27. What’s an opinion you’ve had that has changed over time?

28. Where do you find inspiration?

29. What do you wish someone had taught you a long time ago?

30. Who would be the worst person to get stuck with in an elevator?

31. What do you think is a complete waste of time?

32. What’s considered socially acceptable but really shouldn’t be?

15+ Great Conversation Starters For Networking & Socializing

Conferences and meetings are goldmines for expanding your professional network. So, don’t let your anxiety and shyness hold you back! Take the initiative to spark a conversation with other experts in the field with some of these ice-breakers:

1. Have you come across anything interesting lately?”-

2. What is the nicest conversation or interaction you’ve had at work?

3. Do you prefer in-person or online meetings?

4. What’s the most bizarre excuse you’ve heard for someone coming late to an event or meeting?

5. What’s the funniest thing you’ve ever heard in a meeting?

6. If you were invited to give a TED Talk, what would your topic be?

7. What’s the most amusing email typo you’ve ever made, and how did you deal with it?

8. Have you attended one of these events before?

9. Is this your first time at this venue?

10. If you could choose the venue for the next event, where would it be?

11. Is there anyone here you haven’t met yet?

12. Where would you rather be if not here?

13. What do you hope to discuss at this event?

14. What do you think will be the biggest highlight of this conference?

15. Is there anyone here you think I should meet?

16. Is there anyone you’d like to connect with?

17. What do you think was the most exciting part of the meeting?

18. Will you stay for the whole meeting/conference?

10+ Interesting Conversation Questions For Work Parties & Lunches

Imagine blanking out completely at a work event – a company party or even a casual lunch!  Awkward, right? Yet, these relaxed settings are perfect for friendly chats among coworkers, bringing us closer together. Seize these chances to build rapport with them!

1. Is there anything I can pick up for you while I’m out getting lunch?

2. What are you thinking of ordering?

3. Would you like to share a dessert with me?

4. Do you have any food sensitivities?

5. What’s your favorite dish to whip up?

6. Do you have any great recipes you can share?

7. Do you enjoy dancing? What’s your signature dance move?

8. What favorite food brings back childhood memories for you?

9. If our office had its own wacky mascot, who would it be? What would be their signature saying?

10. If the office held a talent show, what unique skills would we showcase, and would you participate?

11. If the office threw a theme party, what show-stopping costume would you put on, and how would you rock it?

10+ Novelty Conversation Starters For Those Working Remotely

Remote workers can sometimes feel isolated from the team, and keeping conversations flowing through texts can be trickier than face-to-face interactions. That’s where these ice-breakers come in!  They’ll help you build connections and keep your remote colleagues feeling engaged.

1. Have you heard about [news-related events]? How is it impacting your area?

2. What’s something you’re looking forward to this week?

3. What’s the weather like where you are?

4. We have an all-hands meeting next Tuesday. Will you be joining via video?

5. I was really impressed by [a project they handled]. What was the biggest challenge you faced?

6. What’s something you wish more people knew about you?

7. Hey, did you hear we have a new team member? I’m sure you’re going to be interested in this person!

8. What’s your favorite remote work perk?

9. How do you manage to stay active when working from home?

10. Is there anything you miss about working in a traditional office?

11. What’s the most interesting thing you’ve done during a remote workday?

12. Have you attended any virtual events or webinars recently that you found valuable?

13. Do you have a dedicated workspace at home? How do you jazz it up?


Next time you find yourself in an awkward silence, remember to use these witty conversation openers to break the ice. Who knows? You might lighten the mood and keep the conversation smooth sailing. Just remember: we all have our boundaries that one should never cross. So, be selective with your words and questions.

Share on:
Christina J Colclough

Christina J. Colclough

Dr Christina J. Colclough is an expert on The Future World of Work and the politics of digital technology advocating globally for the importance of the workers’ voice. She has extensive regional and global labour movement experience, is a sought-after keynote speaker, coach, and strategist advising progressive governments and worker organisations.

Leave a Comment