1.

What’s something you’ve done that you were really proud of but no one else knows?

What’s something you’ve done that you were really proud of but no one else knows?
2.

Have you ever felt like you had to suppress your opinions to keep the peace?

Have you ever felt like you had to suppress your opinions to keep the peace?
3.

What’s something you’ve done to get attention?

What’s something you’ve done to get attention?
4.

Have you ever felt guilty for wanting to take a break from socializing?

Have you ever felt guilty for wanting to take a break from socializing?
5.

Have you ever regretted a decision you made while upset? What was it?

Have you ever regretted a decision you made while upset? What was it?
6.

Have you ever been in a situation where you felt completely lost?

Have you ever been in a situation where you felt completely lost?
7.

What’s your biggest insecurity in relationships?

What’s your biggest insecurity in relationships?
8.

Have you ever felt pressure to succeed?

Have you ever felt pressure to succeed?
9.

What’s your favorite thing about your best friend?

What’s your favorite thing about your best friend?
10.

What’s your most embarrassing family story?

What’s your most embarrassing family story?
11.

Have you ever been embarrassed by a misunderstanding with a family member?

Have you ever been embarrassed by a misunderstanding with a family member?
12.

Have you ever kept a secret from a partner? Why?

Have you ever kept a secret from a partner? Why?
13.

What’s the most embarrassing thing you’ve ever done while trying to be helpful?

What’s the most embarrassing thing you’ve ever done while trying to be helpful?
14.

What’s your biggest pet peeve about yourself?

What’s your biggest pet peeve about yourself?
15.

What’s the most embarrassing thing you’ve ever done while trying to be funny?

What’s the most embarrassing thing you’ve ever done while trying to be funny?
16.

Have you ever experienced a moment of deep regret? What was it?

Have you ever experienced a moment of deep regret? What was it?
17.

Have you ever lost a bet and had to do something embarrassing?

Have you ever lost a bet and had to do something embarrassing?
18.

What’s the most ridiculous thing you’ve ever done to get someone’s attention?

What’s the most ridiculous thing you’ve ever done to get someone’s attention?
19.

What’s the most embarrassing thing you’ve done for love?

What’s the most embarrassing thing you’ve done for love?
20.

Have you ever struggled to fit in?

Have you ever struggled to fit in?
21.

Have you ever experienced a moment that made you question your values?

Have you ever experienced a moment that made you question your values?
22.

Have you ever had a crush on someone you met through a friend? Did you act on it?

Have you ever had a crush on someone you met through a friend? Did you act on it?
23.

Have you ever felt like you were living someone else’s life?

Have you ever felt like you were living someone else’s life?
24.

Have you ever been caught lying about your feelings? What happened?

Have you ever been caught lying about your feelings? What happened?
25.

Have you ever been in a situation that tested your morals?

Have you ever been in a situation that tested your morals?
26.

Have you ever had a crush on someone you met at work? What did you do?

Have you ever had a crush on someone you met at work? What did you do?
27.

Have you ever cried during a movie?

Have you ever cried during a movie?
28.

What’s something you wish you could change about your communication style?

What’s something you wish you could change about your communication style?
29.

Have you ever felt overwhelmed by the amount of attention you received?

Have you ever felt overwhelmed by the amount of attention you received?
30.

What’s your biggest fear about falling in love?

What’s your biggest fear about falling in love?
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