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 bought a piece of clothing from a thrift store?

👥 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. On have.you, this question draws players from every kind of setting — parties, road trips, dinners, late-night calls — which is why the same question reads differently every time. The interesting part is rarely the answer itself; it is the follow-up, the story behind the yes, or the surprised reaction when someone answers the opposite of what everyone expected.

What do players say?

62%

of players said Yes
21 responses

Based on 21 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 bought a piece of clothing from a thrift store?
→ 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?

Buying a piece of clothing from a thrift store can reveal your sense of style, sustainability values, and willingness to seek unique finds. Curious if you’ve had this experience? Discover what your answers say about you by playing our Have You Ever game.

What This Question Really Asks

This question aims to understand your shopping habits, fashion choices, and attitude toward second-hand shopping. It can spark discussions about ethical consumption or personal style. Exploring this topic can also lead to funny stories about thrift shop adventures or stylish steals. Interested in what other shopping questions we have? Visit our classic questions.

Do you prefer new or vintage clothing?
Are you environmentally conscious in your shopping choices?
Do you enjoy hunting for hidden gems in thrift stores?
Have you found a designer piece at a bargain price?
Would you recommend thrift shopping to others? Check out our categories of questions for more ideas.

How to Use This Question

Setting	Tone	Best for	Tip
Friends game night	Casual and playful	Getting to know each other’s habits	Use lighthearted follow-up questions like funny and embarrassing thrift stories to keep it lively.
First date	Warm and genuine	Sharing personal values and quirky interests	Encourage openness by sharing your own thrift finds and asking about theirs.
Team meeting	Professional but friendly	Building rapport among colleagues	Frame it as a sustainability initiative or hobby that can inspire others to share.
Family dinner	Comforting and engaging	Deepening family bonds	Discuss how thrift shopping fits into your lifestyle and values.
Party	Fun and energetic	Breaking the ice and entertainment	Ask about the best thrift store find they ever made to spark stories and laughter.

When You Say "Yes"

You are likely eco-conscious and care about sustainable fashion.
You enjoy hunting for unique or vintage clothing pieces that stand out.
You’re someone who appreciates good deals and bargains.
You might have a creative side, often customizing thrifted items to fit your style.
You're open to exploring new shopping experiences and support second-hand stores — check out our deep and meaningful questions for more insights.

When You Say "No"

Not having bought from a thrift store might mean you prefer brand-new or store-bought fashion, or perhaps you're unfamiliar with thrift shopping. Alternatively, you might:

Favor shopping at mainstream retail stores or online brands.
Have concerns about clothing hygiene or fit at thrift stores.
Simply haven't had the opportunity to explore thrift shopping yet.

Best Follow-Up Questions

What’s the most interesting item you’ve ever bought second-hand?
Do you have a favorite thrift store or market?
Have you ever thrifted for a costume or themed event?
Would you try thrifting if you haven’t before? Why or why not?
What’s your style inspiration when shopping second-hand?

Need more ideas? Explore our question categories for more inspiration on creating engaging conversations.

Ready to discover more interesting questions? Jump into the game now and involve friends using multiplayer mode for endless fun — let’s see what your stories reveal!

More Money & Shopping Questions

Have you ever saved up for something big and finally bought it?

Play

Have you ever had intense buyer's remorse?

Play

Have you ever returned an item of clothing after you've already worn it?

Play

Have you ever found a significant amount of money on the street?

Play

Have you ever lost your wallet or purse?

Play

Have you ever had your credit card declined?

Play

Have you ever maxed out a credit card?

Play

Have you ever paid for something entirely in coins?

Play

Have you ever haggled or bargained for a lower price at a store?

Play

Have you ever bought something you saw on a late-night infomercial?

Play

Have you ever worked a job you disliked, purely for the money?

Play

Have you ever had a piggy bank you had to break open?

Play

View all Money & Shopping questions →

Suggested Tool

Based on this category

🔀 Category Mixer

📚

All Questions

📂