Does it get awkward about income?

No — questions focus on purchases and habits, not how much anyone earns. Nobody has to disclose numbers.

Mostly yes. Skip a couple of "biggest debt regret" questions if you are using this with colleagues.

Will it depress people?

Surprisingly no — the regret stories tend to be funny rather than sad. Bad-purchase confessions are universal.

Money & Shopping

Have you ever had a garage sale?

👥 Play with Friends

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. Have You Ever questions work because they give everyone the same binary entry point — yes or no — and then let the room decide how far to go. A quick nod counts. A ten-minute story also counts. The format never forces anyone to say more than they want to, which is exactly why people do.

What do players say?

25%

of players said Yes
8 responses

Based on 8 answers so far, 25% of players say yes — making this less common than most people assume.

Discussion starters

→ Who in the group is most likely to have had a garage sale?
→ 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?

Wondering if you've ever organized a garage sale? This question offers a peek into your past experiences with decluttering, selling, and maybe even making a bit of extra cash. Dive into our classic questions category to explore more everyday moments that reveal what makes you tick.

What This Question Really Asks

This question isn’t just about whether you've had a garage sale; it also touches on your attitude towards money, organization, and letting go of possessions. It can also reveal your entrepreneurial spirit or sentimental side. When considering your answer, think about the following:

Are you comfortable parting with your belongings?
Do you enjoy negotiating or bargain-hunting?
Have you ever made a surprising amount of money from a sale?
Would you consider organizing one again? Check out deeper questions for meaningful conversations.
Are you the type to find joy in decluttering or prefer to keep things sentimental?

How to Use This Question

Setting	Tone	Best for	Tip
Friends game night	Casual, fun	Breaking the ice or sharing funny stories	Use this question to find humorous or surprising garage sale stories. Explore funny moments for more laughs.
First date	Light-hearted, flirty	Getting to know each other	Share experiences that reveal personality, like whether you’re thrifty or sentimental, and listen for shared interests.
Team meeting	Professional, relaxed	Build rapport among colleagues	Use this question to learn about colleagues' hobbies or past adventures outside work.
Family dinner	Warm, nostalgic	Sharing personal stories	Encourage family members to reflect on memories associated with their garage sales.
Party	Fun, lively	Enhancing group interaction	This question works well to stir up funny or surprising stories about sales gone wrong or right.

When You Say "Yes"

You’re comfortable letting go of possessions and perhaps even enjoy doing so.
It indicates a practical or entrepreneurial mindset, possibly enjoying barter and negotiations.
You have stories of making money or scoring great deals at garage sales.
You’re open to decluttering and making space in your life.
It suggests you value second chances for items and enjoy thrifty or eco-friendly practices. Check out deep questions to explore what drives your habits.

When You Say "No"

That's okay! Not everyone has experience with garage sales. Maybe you prefer online shopping or donation instead. Alternatively, you haven't had the opportunity or simply don’t find them interesting.

You might not enjoy bargaining or selling.
The idea of parting with belongings may feel sentimental or overwhelming.
Garage sales aren’t part of your lifestyle, but you might still enjoy other money-saving or shopping activities.

Best Follow-Up Questions

What was the most interesting item you ever sold or bought at a garage sale?
Have you ever found a hidden treasure among someone's unwanted items?
Would you rather have a garage sale or donate your stuff? Why?
What’s the funniest or most embarrassing experience you’ve had during a sale?
Do you prefer selling online, hosting yard sales, or using other methods? Find more ideas in our shopping categories.