Have you ever lent money to a friend and never been paid back?

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?

73%

of players said Yes
11 responses

Based on 11 answers so far, 73% 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 lent money to a friend and never been paid back?
→ 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 about the tricky situations that can arise with money and friendships? This question sheds light on your experiences with lending money to friends. Dive into your past and see what it reveals about trust, boundaries, and expectations. Ready to explore more questions like this? Explore questions in the Money & Shopping category.

What This Question Really Asks

This question uncovers your feelings about lending money to friends and whether you’ve experienced the frustration or relief that comes with unpaid debts. It can also reveal how you handle financial trust within your friendships. Classic scenarios often involve situations where money becomes a test of loyalty or boundaries.

How comfortable are you with lending money to friends?
Have you ever experienced a friendship strained over money?
What are your thoughts on loaning money with or without formal agreements?
Have you ever forgiven a debt because you value the friendship?

How to Use This Question

Setting	Tone	Best for	Tip
Friends game night	Casual, light-hearted	Getting to know your friends’ boundaries	Share your own story to encourage openness. Learn more in how to play the game.
First date	Playful yet meaningful	Discovering values and financial perspectives	Use this question to spark deep conversations about trust.
Team meeting	Professional, respectful	Understanding colleagues’ views on borrowing	Approach with sensitivity—money can be a sensitive topic.
Family dinner	Warm, honest	Talking about family financial traditions	Encourage sharing stories about family lending experiences.
Party	Fun, relaxed	Light teasing about past money mishaps	Keep it playful—avoid making it a heavy discussion.

When You Say "Yes"

You’re comfortable trusting friends with your money and believe in giving second chances.
You have experienced forgiving a debt because keeping the friendship was more important than the money.
You believe that lending money can strengthen bonds if managed properly.
You’re open to discussing money openly, even when it’s uncomfortable.
You consider the person’s character and history when deciding whether to lend.

If this resonates with you, explore more deep and meaningful questions to better understand your relationships.

When You Say "No"

Saying no to lending money can be a way to set healthy boundaries and protect yourself from potential hurt. It could also reflect a personal stance on financial independence or past experiences with unpaid debts.

You prefer to avoid risking friendship over money.
You have had negative experiences with friends not paying back loans.
You believe money matters should be handled cautiously to prevent misunderstandings.

Best Follow-Up Questions

Have you ever regretted lending money to someone?
How do you set boundaries when it comes to lending or borrowing?
What’s the biggest money-related lesson you’ve learned from friends?
Have you ever borrowed money from a friend? How did it go?
Would you prefer to avoid money talks altogether in friendships? Why?

Find more engaging questions in the Money & Shopping category, or try building your own with our custom question builder.

Ready to turn this into a game? Jump into the game platform and challenge your friends. For group play, check out multiplayer options to see who’s most likely to lend money and never get paid back.

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