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 felt intense guilt after spending a lot of money?

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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. The yes-or-no format is what makes it work — nobody has to volunteer a story, but once someone says yes the room always wants to hear it. That is why this question comes up again even in groups that have played before: the answer changes, the story changes, and the same question lands differently every time someone new is in the room.

What do players say?

90%

of players said Yes
21 responses

Based on 21 answers so far, 90% of players say yes — making this one of the most common experiences players own up to.

Discussion starters

→ Who in the group is most likely to have felt intense guilt after spending a lot of money?
→ 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?

Feeling guilty after indulging in a big purchase is a common experience that often reveals your inner financial mindset. Explore this emotion and uncover more about your spending habits by diving into questions about money & shopping with the game.

What This Question Really Asks

This question probes your relationship with money and how your conscience reacts to financial decisions. It helps uncover deeper feelings about spending, responsibility, and self-control. Sometimes, it sparks insights into financial habits or emotional responses tied to money, which can lead to meaningful conversations.

Do I experience regret when I make large purchases?
Are my spending habits driven by emotions or needs?
How do I justify expensive expenditures to myself?
Can guilt influence my future spending decisions? Check out other question categories for more themes.

How to Use This Question

Setting	Tone	Best for	Tip
Friends game night	Light-hearted and playful	Getting to know each other's money stories	Use humor and share your own experiences to keep it engaging.
First date	Thoughtful and empathetic	Building trust and understanding	Frame the question as part of a story or personal anecdote — more details at how to play.
Team meeting	Serious and reflective	Deepening team bonds and financial transparency	Encourage sharing without judgment, promoting openness.
Family dinner	Supportive and warm	Discussing financial values and lessons	Be sensitive to different perspectives about money.
Party	Fun and surprising	Light conversation starters	Now’s a good time to liven up the mood with funny or embarrassing questions.

When You Say "Yes"

You might feel guilty about spending beyond your means and worry about debt or financial insecurity.
You understand the importance of budgeting and saving, believing that impulsive purchases aren't aligned with your financial goals.
You may have a history of financial mistakes that make you more sensitive to spending guilt.
You take responsibility for your financial decisions and want to improve your money habits.
Financial guilt can be a sign that you genuinely care about your well-being and want to make better choices, as discussed in money & shopping.

When You Say "No"

Not feeling guilty might mean you view spending as a positive or neutral act. You trust your financial judgment and do not experience regret over big purchases.

You feel confident about your spending decisions.
You prioritize enjoying life without excessive worry about money.
You may have a solid financial plan that supports your spending habits.

Best Follow-Up Questions

What was the most expensive purchase you ever made that made you feel amazing?
Do you set a budget before making large purchases?
How do you decide whether a purchase is worth feeling guilty over?
Have your feelings about money changed over the years?
What advice would you give someone struggling with guilt related to spending?

Explore more about personal finance and emotional spending with our categories to deepen your money conversations.

Tip: Use our game to spark honest conversations about money, or try playing with friends to see different perspectives. Building a custom set with your own questions can make sessions even more engaging.

More Money & Shopping Questions

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

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Have you ever had intense buyer's remorse?

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

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

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Have you ever lost your wallet or purse?

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Have you ever had your credit card declined?

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Have you ever maxed out a credit card?

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Have you ever paid for something entirely in coins?

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

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

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

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

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View all Money & Shopping questions →

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