Have you ever sold something you owned on Craigslist, eBay, or Facebook Marketplace?

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. What makes this format durable is that a no can be just as interesting as a yes. 'No, but I once…' or 'No, and here is why not' opens a conversation the question never directly asked for. The best sessions are ones where the follow-up runs longer than the question itself.

What do players say?

57%

of players said Yes
7 responses

Based on 7 answers so far, 57% 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 sold something you owned on Craigslist, eBay, or Facebook Marketplace?
→ 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?

Discovering Your Sales Secrets: How Well Do You Know Your Selling Stories?

This question dives into your experiences with selling personal belongings online, revealing how comfortable and confident you are in navigating digital marketplaces like Craigslist, eBay, or Facebook Marketplace. Whether it sparks nostalgic stories or uncomfortable memories, exploring your past sales adventures can lead to fun and revealing conversations. Ready to explore your selling milestones? Start playing and see what stories unfold!

What This Question Really Asks

This question is not just about transactions; it’s about your comfort level with selling items and the stories behind those moments. It uncovers whether you’ve experienced success, stumble, or surprises in the digital marketplace. Could it be a sign of how you handle change or adapt to new environments? By exploring this, you can open pathways to deeper stories about risk-taking or resourcefulness.

Have you taken a risk by selling something valuable you once owned
Are you comfortable negotiating or setting your own prices
Do you remember a particularly funny or embarrassing selling story
Learn about your approach to decluttering and letting go of possessions
Discover if you're more of a thrifter or a collector at heart through your selling habits

How to Use This Question

Setting	Tone	Best for	Tip
Friends game night	Light-hearted, humorous	Breaking the ice or sharing funny stories	Use personal anecdotes to keep the mood fun and engaging
First date	Honest, slightly flirty	Getting to know each other's past experiences	Relate your experience to a memorable moment — funny or embarrassing stories work well here
Team meeting	Professional but personable	Building rapport with colleagues	Share a story that highlights your resourcefulness or adaptability
Family dinner	Casual and warm	Sharing personal growth stories with relatives	Reflect on how selling helped you declutter or make thoughtful decisions
Party	Playful and fun	Creating lively conversations	Turn it into a humorous recount of a funny selling experience — it keeps everyone entertained

When You Say "Yes"

You’ve sold something on an online marketplace and felt accomplished.
You've experienced a funny or awkward moment during a sale.
You feel confident negotiating prices or buyer interactions.
You've decluttered your space significantly through selling.
You understand the value of personal sales as a form of entrepreneurship or resourcefulness, like when exploring Money & Shopping.

When You Say "No"

That’s completely okay! Maybe you haven’t sold anything online yet, or perhaps selling isn’t your thing. Not every experience has to involve online sales, and that’s perfectly fine.

You might prefer giving away items or donating rather than selling.
You have not yet tried selling through online platforms but are curious.
You’re more comfortable shopping than selling.

Best Follow-Up Questions

What was the most memorable item you sold and why?
Have you ever had a funny or awkward encounter with a buyer?
What motivates you to sell or declutter your space?
Would you try selling again? Why or why not?
What’s the most valuable thing you’ve ever sold?

Explore more questions about Money & Shopping or use our group decider to pick your perfect conversation starter.

Remember, sharing stories about selling or shopping can be hilarious and revealing — give our game a try and invite friends to join in the fun! For group play, check out multiplayer options.

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