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 high-end designer item?

👥 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?

67%

of players said Yes
12 responses

Based on 12 answers so far, 67% 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 high-end designer item?
→ 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 splurged on a luxurious designer item? This question uncovers stories of indulgence, taste, and perhaps a little impulse shopping. For more insights into luxury and spending habits, check out our categories.

What This Question Really Asks

This question dives into your personal experiences with high-end shopping and reveals your attitude towards luxury brands. It can lead to stories about your most extravagant purchases or your reasons for skipping designer labels. When exploring personal spending, it’s interesting to see how it reflects your self-image or aspirations. To better understand spending behaviors, you might want to look into classic money questions.

Have you ever felt the pull of luxury shopping and given in?
Did purchasing a high-end designer item happen on a special occasion or as a treat?
Are you more about quality than brand names when it comes to shopping?
Have you ever regretted buying a pricey designer product later?
Would you tell others if you had purchased an expensive designer item? Explore more deep questions for meaningful conversations.

How to Use This Question

Setting	Tone	Best for	Tip
Friends game night	Playful & relaxed	Breaking the ice, laughs & stories	Use this question to spark funny or surprising stories about luxury tastings. Check out group decider for fun ways to choose questions.
First date	Interested & sincere	Getting to know each other's lifestyles	Frame it as curiosity about shared values instead of judgments. Visit categories to find similar questions.
Team meeting	Professional but personal	Building rapport among colleagues	Keep it light and respectful—avoid making assumptions. For team-building ideas, see our custom question sets.
Family dinner	Warm & engaging	Sharing personal stories and values	Ensure a comfortable environment; not everyone may want to share. Check out funny family questions for more.
Party	Energetic & fun	Getting everyone involved	Throw in humorous follow-ups to spice up the mood. Start playing here!

When You Say "Yes"

You enjoy treating yourself and celebrate achievements with luxury purchases.
You have an eye for style, and quality matters more than price.
You've experienced the thrill of unboxing or wearing your designer item.
You feel confident and proud when sporting high-end accessories or clothing.
Discussing your designer purchases reveals your appreciation for craftsmanship or status, like in meaningful conversations.

When You Say "No"

Not purchasing designer items might suggest you prefer practicality or value. It could also indicate a focus on experiences over possessions. Some possibilities include: