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Why people ask this
This question works because the yes-or-no split always surprises the room — someone answers in a way nobody expected, and the conversation starts from there. Money is the topic everyone pretends not to care about and then answers fastest — questions like this make the regrettable purchases come out. Questions like this one get played across every kind of group on have.you — couples on a first date, coworkers at team events, friends on long drives. Each setting produces a different answer, which is part of why Have You Ever has stayed in circulation long after most party games get retired.
What do players say?
8 responses
Based on 8 answers so far, 62% of players say yes — making this something the majority of players have actually done.
Discussion starters
- → Who in the group is most likely to have started a side hustle to make extra cash?
- → What's the full story — and who in the group is most surprised by your answer?
- → What is the most expensive thing you have ever returned?
- → What do you spend more on than you should?
- → What item do you regret buying the most?
If you're curious about the entrepreneurial spirit behind side jobs, this question uncovers your motivations and experiences in making extra cash. Want to explore more about day-to-day questions that reveal personal habits? This is a great one to get insight into your own and others' financial journeys.
What This Question Really Asks
This question inquires whether you've ever taken steps outside your primary job to earn additional income. It aims to reveal your entrepreneurial spirit, motivation, and willingness to explore new opportunities. By reflecting on this, you can understand more about your financial goals or creative pursuits. If you're interested in deeper conversations about life choices, check out deep and meaningful questions. Considering this helps gauge your comfort level with risk and your drive for independence.
- Have you ever tried to earn money on the side?
- Are you open to new business ideas or freelance opportunities?
- How motivated are you to supplement your income?
- Do you enjoy the challenge of balancing multiple projects?
- Are you curious about starting your own side hustle someday? Explore other question categories for more insightful topics.
How to Use This Question
| Setting | Tone | Best for | Tip |
|---|---|---|---|
| Friends game night | Casual, playful | Getting to know each other's ambitions | Encourage sharing stories about side hustles to spark laughs and connection (group decider helps choose the best questions). |
| First date | Warm, sincere | Building trust and understanding | Use this to explore future goals—be open and listen attentively to their experiences. |
| Team meeting | Professional, insightful | Understanding colleagues' passions | Ask about side projects to foster team bonding and mutual support. |
| Family dinner | Light, honest | Sharing personal stories | Use this question to learn about family members' hidden talents or entrepreneurial dreams. |
| Party | Fun, lively | Ice-breaking and laughs | Share your own side hustle stories to encourage others to open up as well. |
When You Say "Yes"
- You’ve actually started a side hustle, like selling crafts or freelance work.
- You’re actively looking for new ways to earn extra cash.
- You enjoy the freedom and flexibility that comes with additional income streams.
- You see your side gig as a potential full-time opportunity someday.
- You’ve learned valuable skills or connections through your side hustle. For more on building financial independence, explore funny and embarrassing moments.
When You Say "No"
Saying no might mean you haven't pursued a side hustle yet or you're not interested in additional responsibilities outside your main job. It could also mean:
- You prefer focusing on your current career path without distractions.
- You haven't found a side hustle that truly excites you.
- Financial goals are different for you.
Best Follow-Up Questions
- What motivated you to start your first side hustle?
- What are some challenges you've faced with balancing your main job and side projects?
- Would you recommend others try to start a side business?
- How has your perspective on money changed since you started?
- What would you do differently if you started your side hustle again?
Looking for more ways to spark meaningful conversations? Check out question categories or use our icebreaker generator for fun ideas.
Thinking of sharing this question with friends? Use our play page to start the game now, or invite friends to join via multiplayer mode for added fun and engagement!
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