1.
What’s the most embarrassing thing you’ve ever done to make someone laugh?
What’s the most embarrassing thing you’ve ever done to make someone laugh?
2.
Have you ever felt uncomfortable expressing your true opinions?
Have you ever felt uncomfortable expressing your true opinions?
3.
Have you ever been rejected in a way that made you feel terrible? What happened?
Have you ever been rejected in a way that made you feel terrible? What happened?
4.
What’s the most embarrassing thing you’ve ever done at a family gathering?
What’s the most embarrassing thing you’ve ever done at a family gathering?
5.
Have you ever felt judged for your choice of career?
Have you ever felt judged for your choice of career?
6.
What’s something you wish you could say to your ex?
What’s something you wish you could say to your ex?
7.
What’s the worst gift you’ve ever given?
What’s the worst gift you’ve ever given?
8.
What’s something you wish you could say to someone who has let you down?
What’s something you wish you could say to someone who has let you down?
9.
What’s something you’re really bad at that surprises people?
What’s something you’re really bad at that surprises people?
10.
What’s the biggest risk you’ve ever taken in a relationship?
What’s the biggest risk you’ve ever taken in a relationship?
11.
Have you ever experienced a moment of clarity during a difficult time?
Have you ever experienced a moment of clarity during a difficult time?
12.
Have you ever had a crush on someone you met while traveling?
Have you ever had a crush on someone you met while traveling?
13.
What’s the most ridiculous excuse you’ve ever given for being tired?
What’s the most ridiculous excuse you’ve ever given for being tired?
14.
What’s something you wish you could tell someone who has been critical of you?
What’s something you wish you could tell someone who has been critical of you?
15.
Have you ever felt pressured to hide your true feelings from someone?
Have you ever felt pressured to hide your true feelings from someone?
16.
What’s your favorite way to relax?
What’s your favorite way to relax?
17.
What’s something you wish you could change about the way you were raised?
What’s something you wish you could change about the way you were raised?
18.
What’s your most embarrassing memory?
What’s your most embarrassing memory?
19.
What’s something you wish you could change about your daily routine?
What’s something you wish you could change about your daily routine?
20.
What’s something you wish you could do to make a difference in the world?
What’s something you wish you could do to make a difference in the world?
21.
What’s something you did as a child that you’re embarrassed about now?
What’s something you did as a child that you’re embarrassed about now?
22.
What’s your biggest fear about being vulnerable with someone?
What’s your biggest fear about being vulnerable with someone?
23.
What’s the most ridiculous excuse you’ve ever given to avoid an event?
What’s the most ridiculous excuse you’ve ever given to avoid an event?
24.
What’s something you wish you could say to someone who inspires you?
What’s something you wish you could say to someone who inspires you?
25.
What’s your most cherished childhood possession?
What’s your most cherished childhood possession?
26.
What’s something you’re really bad at?
What’s something you’re really bad at?
27.
What’s something you wish you could change about how you handle criticism?
What’s something you wish you could change about how you handle criticism?
28.
Have you ever had a crush on someone who didn’t feel the same way? What did you do?
Have you ever had a crush on someone who didn’t feel the same way? What did you do?
29.
What’s something you wish you could change about your relationship with your parents?
What’s something you wish you could change about your relationship with your parents?
30.
Have you ever been embarrassed by your choice of food at a restaurant?
Have you ever been embarrassed by your choice of food at a restaurant?
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