1.

What’s something you wish you could tell your friends about your dreams and ambitions?

What’s something you wish you could tell your friends about your dreams and ambitions?
2.

What’s something you wish you could tell your friends about your passions?

What’s something you wish you could tell your friends about your passions?
3.

What’s something you wish you could tell your friends about your past mistakes?

What’s something you wish you could tell your friends about your past mistakes?
4.

Have you ever had to deal with a difficult coworker?

Have you ever had to deal with a difficult coworker?
5.

What’s the most embarrassing thing you’ve ever done to get out of a situation?

What’s the most embarrassing thing you’ve ever done to get out of a situation?
6.

Have you ever felt overwhelmed by someone else’s expectations of you?

Have you ever felt overwhelmed by someone else’s expectations of you?
7.

What’s the most embarrassing thing you’ve ever done during a job interview?

What’s the most embarrassing thing you’ve ever done during a job interview?
8.

Have you ever experienced a moment where you realized who your true friends are?

Have you ever experienced a moment where you realized who your true friends are?
9.

Have you ever kept a secret from a friend? What was it?

Have you ever kept a secret from a friend? What was it?
10.

What’s your biggest regret in your career?

What’s your biggest regret in your career?
11.

Have you ever felt judged for your choice of partner?

Have you ever felt judged for your choice of partner?
12.

What’s something you wish you could tell your friends about your insecurities?

What’s something you wish you could tell your friends about your insecurities?
13.

What’s your biggest fear about losing a loved one?

What’s your biggest fear about losing a loved one?
14.

What’s something you wish you could change about your approach to conflict?

What’s something you wish you could change about your approach to conflict?
15.

What’s the most embarrassing moment you’ve had in front of your family?

What’s the most embarrassing moment you’ve had in front of your family?
16.

Have you ever been embarrassed by a mistake made during a performance?

Have you ever been embarrassed by a mistake made during a performance?
17.

Have you ever felt judged for your choice of career?

Have you ever felt judged for your choice of career?
18.

Have you ever felt guilty for not being honest with someone close to you?

Have you ever felt guilty for not being honest with someone close to you?
19.

What’s the most embarrassing thing you’ve ever done while trying to impress a crush?

What’s the most embarrassing thing you’ve ever done while trying to impress a crush?
20.

Have you ever been embarrassed to admit your hobbies?

Have you ever been embarrassed to admit your hobbies?
21.

What’s the most embarrassing thing you’ve ever done at work?

What’s the most embarrassing thing you’ve ever done at work?
22.

What’s your biggest fear about love?

What’s your biggest fear about love?
23.

Have you ever had a bad breakup?

Have you ever had a bad breakup?
24.

What’s the most ridiculous thing you’ve done in the name of love?

What’s the most ridiculous thing you’ve done in the name of love?
25.

Have you ever lied about your age? Why?

Have you ever lied about your age? Why?
26.

What’s something you wish you could tell your friends about your hopes and dreams?

What’s something you wish you could tell your friends about your hopes and dreams?
27.

Have you ever been caught daydreaming during a lecture? What happened?

Have you ever been caught daydreaming during a lecture? What happened?
28.

What’s your biggest fear about being vulnerable in a relationship?

What’s your biggest fear about being vulnerable in a relationship?
29.

What’s the most difficult conversation you’ve ever had to initiate?

What’s the most difficult conversation you’ve ever had to initiate?
30.

What’s something you wish you could tell your younger self about relationships?

What’s something you wish you could tell your younger self about relationships?
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