50 Funny Questions to Ask Your Principal

Imagine if you are hired as an MC for your high school reunion and your principal will be there, or a group of principals is having a small party and you’ve been called to MC, what funny questions can you ask to keep everyone laughing and interested?

If that is the case and you are in high school or have passed through high school, there are some funny questions you had asked or wished to ask your principal, and you would want to use that to have some fun during the event.

Maybe you were bold enough to either ask those questions and get away with it, or not get away with it or you chickened out and refused to take the bold step. That aside, you finally have the opportunity to use those questions you have in mind.

Nevertheless, whoever said that you cannot crack some light-hearted jokes with your principal has not read this article ‘cause in this article we have compiled fifty (50) funny questions to ask your principal.

50 Funny Questions to Ask Your Principal

1. If you could go back to teaching, what subject would you like to teach? When you’ve selected the subject, would you love to be giving your students difficult assignments every day? (Most principals got into that position from being teachers, so this is a way to find out if they enjoyed active teaching.)
2. What’s the most ridiculous excuse any student has ever given after they were sent to your office? If you were to create another room where students would be sent for misbehaving, what would you call it?
3. If you were to be given one superpower to help you handle students, what would you want it to be? Could you explain in detail which student you would use that superpower on and what you would do to him/her?
4. If any teacher or student does something hilarious, how do you manage to keep a straight face? Can you share an experience when this happened and how you were able to control your laughter? (It’s not always easy to keep up the professionalism when something hilarious happens, so this is a way to test how professional they are as principals in a funny way.)
5. If you could have a day off to do something that is absolutely not school-related, what would you do? That is, is there something that you would prefer doing the whole day if you were not a principal?
6. How do you handle dealing with students and then go back home to deal with your children’s tantrums? Have you ever taken out a bad day on your children or given them punishments that you would normally give your students?
7. What favorite snacks do you enjoy the most but are actually meant for students? Are there snacks that you eat and enjoy but you know are meant for children? Also, are there children’s snacks that you’ve come to enjoy from working as a principal?
8. What weird student stuff do you do behind closed doors but will never be caught dead doing in front of students? Like, do you have a goofy self that you will never be caught dead showing your students?
9. If there were no regulations on punishments for students, what punishment would you give to students sent to your office aside from detention? Do you think that most times the punishments given to students do not fit the crime (as in, it’s lesser)? For instance, some students are quite impossible to deal with and instead of detention maybe they can serve a tougher punishment that will leave a more permanent transformation.)
10.  When you want to let go during karaoke with the teachers, what is your go-to song? Have you ever gotten drunk and sang so joyously before your teachers after pretending to be strict? (With just a few shots of alcohol and the right ambiance, your principal may tend to loosen up so this question helps you tap into that information.)
11.  If you were to choose a mascot for the football team based on your childhood fantasies, what would it be? Have you ever done mascot services during a football match without the students knowing?
12.  What normal thing about your life outside school do you wish both students and teachers knew? Is there something that you have ever been doing that made you think ‘Oh, I wish these people were here to see this’?
13.  If your teachers were to take exams and you were to grade them, who do you think would score the highest? Have there ever been a competition held amongst teachers and how was the winner determined?
14.  What did you do to your principals as a student in high school that you’re afraid your students will do to you? Do you believe in karma and do you think some mischievous things you’ve done in the past will be done to you?
15.  Between the nickname you gave your principal when you were in high school and the one students have given you now, which one do you think is more hilarious? Do you know how your nickname came about and who started calling you such a name?
16.  How do you feel as a principal when you are making an important announcement at the school assembly and students are whispering to each other? Have you ever had to scream to get students’ attention cause they were talking over you?
17.  How do you put yourself on timeout when you are asked to handle students whom even God cannot handle? That is, have you ever met students who are so difficult that you are sure the Lord Himself wouldn’t want to handle such students?
18.  What’s the weirdest request a parent has ever made to you concerning their child who is a student in your school? Do you think parents see you as a miracle worker who makes impossible requests sometimes?
19.  During the parent and teachers meeting, how do you handle impossible and entitled parents? Have you ever had to be so firm with parents that they were shocked ‘cause you are usually friendly?
20.  What type of miracles have parents asked you to perform to improve the performance of their child(ren) who is not doing well in school? Have you ever met students who are so bad at academics that you almost advised them to drop out?
21.  Do you think if you were to play a light-hearted prank on parents they would share in your sense of humour and laugh about it? Have you ever tried and what happened – did you almost get into trouble for taking it too far?
22.  What craziest prank have you ever thought of, that you’re sure will get you fired if you try it out? Who did you think of using the prank on – parents, teachers, or students?
23.  Have you ever screwed up so bad but got away with it just because you are the principal? Are there mistakes that you’ve made that you know if you were not a principal, you would have gotten in trouble for?
24.  What compliments have students ever given you that you were sure were just disguised insults? For instance, have you worn a particular piece of clothing or cut a particular style of hair that had students complimenting you, but deep down you were sure they were insults?
25.  As a principal, what body part won’t you mind losing to make your job easier but still won’t make it any more tolerable? If you were to trade something valuable to make your job more enjoyable, what would it be?
26.  Do you do your job because you love it and are good at it or because you need the money? And if you were to choose to do something else, what would you rather do? (80% of people in the labor force are not doing the job they love, they are doing the job that pays the bills. So, this question allows you to know which category the principal falls into.)
27.  Who is the messiest teacher and/or student that you know and did you ever think that they were related? Were you ever so convinced that two of your students were related but they were not and vice versa?
28.  What’s the silliest reason that made a parent threaten to sue the school? When they realized that they couldn’t sue the school for such a silly reason, were you obvious with how satisfied you were?
29.  What is the dumbest way that a student has injured you and how did you handle it? Have you had a student intentionally hurt you and you wanted to hurt them back so bad but you just had to remind yourself that they are children?
30.  Have you ever had any reason to speak to a parent rudely and what prompted it? After you spoke to them, did you make an effort to apologize or were you like f**k them?
31.  Do you have a student that you really hate but can’t do anything about them because of their parent’s status? Like, is there a student that you are sure if they didn’t have the protection of their parents they would have served so much punishment?
32.  Have you ever had to tell a parent off and how satisfied were you when you finally spoke up for yourself? Can you tell us in deets the reaction of the parents and if you regretted your action?
33.  How do your children react to having a parent who is a principal? Like do they pretend not to know you and all that stuff? Do they have certain privileges just from being the principal’s children and have you intentionally done anything to embarrass them?
34.  If any of your kids get in trouble and are brought to your office, how do you play both the role of parent and principal to them? Do they get punished extra for being truant or even grounded (if they are teenagers)?
35.  What’s the most sarcastic reply you’ve given to a student/parent/teacher when they asked you an obvious/unintelligent question? Have any student or parent frustrated you by repeatedly asking questions you’ve already given explanation to?
36.  What’s the question you’ve been prepared to answer as a principal but no student/teacher has ever thought to ask you? Have you ever been preparing for a moment where you’ll be asked a question that will put you in the spotlight but no one ever got around to it?
37.  If the opportunity presents itself, what is that one thing you’ve always wanted to say or do as a principal? That is, if you were not limited in any way, what would you wish to achieve? (Rules were created for some reasons, and if it was not there, how wild would one be? Let’s find out!)
38.  Do you have a favorite student and is it the fact that they are not crazy that makes them your best? Teenagers can be a handful so what makes this one special – the fact that they are old-fashioned?
39.  Is the way you punish students when they are sent to your office the same way you punish your wife/husband at home? (Wink!) (This particular question is a bit kinky and should be asked by an adult in an acceptable social setting.)
40.  While you are trying to be a great example, are there things you’ve learned from your students in all your years as a principal? Seeing that we are living in the Gen Z era, are there things that your students have taught you that amazed you?
41.  Have any of your students ever openly confessed to having a crush on you and how did you handle it? Do you tone down your hotness with old-fashioned clothes to avoid looking too attractive to students/parents?
42.  Have you ever had a student or parent in your office who farted and it smelt so bad? How did you handle such a situation without necessarily embarrassing the parent or student?
43. Have any students ever asked you an intrusive question that others were too afraid to ask you directly? Is there any bold student who has ever said their minds or asked a question that you are sure was on other students’ minds but they were afraid to ask?
44. Has there ever been an absurd rumor that was spread about you and how were you able to stop the rumors from spreading? That is, have you ever come in to work only to be told the most insane rumor about you?
45. Have you ever stood in for any of your teachers who called in sick and found it difficult to teach or keep the class under control? Did you ever assume that teaching is harder than being a principal till you experienced it?
46. Do you think your method of handling students is the best and most effective method? If yes, why then are the students still truant and why do they still hate school?
47. Have you ever been secretly happy when a student ‘took care’ of his/her bully but outwardly you were claiming that there are more civil ways to handle such situations? It’s always hard to tame bullies especially if their parents are influential, so have you ever been secretly excited when a victim took care of his/her bullies?
48.  Have parents ever lost it and fought each other in your office? What did they destroy and were you able to get them to pay for damages? If it’s not so intrusive, can you give us the tea of what happened that caused the fight?
49. Do you claim not to be biased but have a student that you favor above others? If yes, what makes you prefer them, and will you ever openly admit to being biased? Can you give us an example of when that happened and if the other students noticed what you did?
50. What is the biggest failure you have ever experienced as a principal? How did you handle and what did you learn from such a situation? The aim is to learn a thing or two from them while getting them to share an interesting part of their journey.

Finally

These questions are not only hilariously harmless, but they are also great conversation starters to create a great relationship with your principal.

Some funny questions can also be asked in social settings to get everyone laughing and make socializing easier. However, be sure that the principal has a sense of humor, or they will find these questions insulting instead of entertaining.

The idea is to humor them by asking questions that will get them to share a hilarious experience. Some questions can only be asked if you’re already an adult and you are in an event that equally has adults in attendance.

Hence, it’s left for you to filter questions to ask.