20 Questions

Juicy Questions to Ask Your Cousin

Fun, engaging questions to spark interesting conversations and learn more about your cousin's life, experiences, and personality.

1

What's the most embarrassing thing that's ever happened to you?

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Why this works

Creates laughter and bonding through shared vulnerability while revealing their sense of humor and ability to laugh at themselves.

2

If you could have dinner with anyone living or dead, who would it be and why?

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Why this works

Reveals their interests, values, and intellectual curiosity while being universally engaging and thought-provoking.

3

What's the wildest thing you've ever done that you probably shouldn't have?

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Why this works

Encourages sharing of adventurous experiences and reveals their risk-taking personality and sense of adventure.

4

If you could switch lives with anyone for a day, who would it be?

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Why this works

Shows their aspirations and reveals what kind of life or experiences they find appealing or intriguing.

5

What's the most ridiculous lie you've ever told that people actually believed?

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Why this works

Creates humor and reveals their creativity and storytelling ability while showing their playful side.

6

If you could have any superpower, what would it be and how would you use it?

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Why this works

Reveals their personality and values through their choice of power and how they would use it, showing their character and priorities.

7

What's the weirdest dream you've ever had?

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Why this works

Creates interesting conversation and reveals their subconscious thoughts and creativity while being entertaining and memorable.

8

If you could go back in time and change one thing, what would it be?

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Why this works

Reveals their regrets, values, and what they consider important while showing their reflective nature and life lessons learned.

9

What's the most expensive thing you've ever bought that you probably shouldn't have?

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Why this works

Creates relatable conversation about spending habits and reveals their values around money and material possessions.

10

If you could be famous for anything, what would you want to be known for?

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Why this works

Reveals their aspirations and what they value most while showing their ambitions and sense of purpose.

11

What's the strangest food combination you actually enjoy?

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Why this works

Creates light, fun conversation while revealing their adventurous eating habits and willingness to try new things.

12

If you could read minds for one day, whose mind would you want to read?

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Why this works

Reveals their curiosity about others and shows who they find most interesting or mysterious in their life.

13

What's the most awkward situation you've ever been in?

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Why this works

Creates bonding through shared awkwardness and reveals their ability to handle uncomfortable situations with humor.

14

If you could have any job in the world, what would it be?

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Why this works

Reveals their career aspirations and interests while showing what kind of work they find appealing or meaningful.

15

What's the weirdest habit you have that most people don't know about?

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Why this works

Creates intimacy through sharing personal quirks and reveals their unique personality traits and idiosyncrasies.

16

If you could live anywhere in the world, where would you choose?

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Why this works

Reveals their travel aspirations and preferences while showing what kind of lifestyle or environment appeals to them.

17

What's the most ridiculous thing you've ever done to impress someone?

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Why this works

Creates humor and reveals their romantic or social interests while showing their willingness to go to extremes for others.

18

If you could have any animal as a pet, what would you choose?

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Why this works

Reveals their personality through their choice of animal and shows their preferences for companionship and care.

19

What's the most interesting thing you've learned recently?

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Why this works

Shows their intellectual curiosity and interests while revealing what kind of information or topics they find engaging.

20

If you could have a conversation with your younger self, what advice would you give?

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Why this works

Reveals their life lessons and wisdom while showing their growth and self-reflection abilities.

Best Practices for Fun Family Conversations

Expert tips and techniques for getting the most out of these questions.

Best Practices

Create a Safe, Non-Judgmental Environment

Ensure your cousin feels comfortable sharing by being supportive and non-critical. Family relationships thrive on acceptance and understanding.

Share Your Own Stories First

Lead by example by sharing your own experiences and stories. This creates a reciprocal environment where both of you feel comfortable opening up.

Keep the Mood Light and Fun

While some questions may touch on deeper topics, maintain a playful, curious tone that encourages sharing without pressure or judgment.

Question Sequences

The Embarrassing Stories Sequence

1
What's the most embarrassing thing that's ever happened to you?
2
What's the most awkward situation you've ever been in?
3
What's the most ridiculous lie you've ever told?
4
What's the weirdest habit you have?

The Aspirations and Dreams Sequence

1
If you could have any job in the world, what would it be?
2
If you could be famous for anything, what would you want to be known for?
3
If you could live anywhere in the world, where would you choose?
4
If you could have any superpower, what would it be?

Common Pitfalls

Don't Judge or Criticize

Avoid making negative comments about their answers or experiences. The goal is to create a safe space for sharing and bonding.

Don't Push Too Hard

If someone seems uncomfortable with a question, don't pressure them to answer. Respect their boundaries and move on to something else.

Don't Use Information Against Them

Never use the information shared in these conversations against your cousin later. These conversations are about building trust and connection.

Conversation Templates

The Fun and Games Approach

1
Step 1: Start with: "What's the most embarrassing thing that's ever happened to you?"
2
Step 2: Follow with: "What's the wildest thing you've ever done?"
3
Step 3: Deepen with: "What's the weirdest dream you've ever had?"
4
Step 4: Conclude with: "What's the most ridiculous thing you've ever done to impress someone?"

The Aspirations and Dreams Approach

1
Step 1: Begin with: "If you could have any job in the world, what would it be?"
2
Step 2: Explore with: "If you could be famous for anything, what would you want to be known for?"
3
Step 3: Investigate with: "If you could live anywhere in the world, where would you choose?"
4
Step 4: Clarify with: "If you could have any superpower, what would it be?"

Further Reading

"The Art of Conversation" by Catherine Blyth
"How to Win Friends and Influence People" by Dale Carnegie
"The Charisma Myth" by Olivia Fox Cabane

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