Funny Questions to Ask Pledges
Twenty harmless icebreakers for fraternity or sorority pledges, written for laughs rather than pressure: which kitchen appliance they would be, the food combination they defend, their most useless talent, and the strangest thing in their room right now.
The questions
Open any question for the note
If you could be any kitchen appliance, which one would you be and why?
Why ask it
A good first question because it is impossible to answer badly and nobody has to reveal anything. Whoever picks a toaster and explains why in one sentence sets a friendly tone. Whoever overthinks it gets a laugh for that instead.
What's the weirdest food combination you actually like?
Why ask it
Instant disagreement, which is what you want early on. It also means the room learns something specific about each person in four words, and half of them will end up defending their answer to a stranger.
What's your most useless talent? Can you show us?
Why ask it
The demonstration is the point, and it turns an answer into two minutes of entertainment. Keep it fully optional. Nobody should feel they are being asked to perform on demand, which is a line this kind of setting can cross without noticing.
What's the most random fact you know that has never once been useful?
Why ask it
This lets quieter people contribute something impressive without talking about themselves at all. Expect facts about animals, space and dead monarchs. Somebody will fact-check it on their phone, which is fine and usually funnier.
If you could only have one condiment for the rest of your life, which would it be?
Why ask it
Fast, unanimous participation, and a rare question where nobody needs thinking time. Good to drop in when energy dips, and good for a large group where you need twenty answers in three minutes.
Which three emojis do you use the most?
Why ask it
People can check their own phone, so the answers are honest rather than curated. It also produces the first genuine surprise about someone, because the three nobody would have guessed always belong to the quietest person in the room.
What's the worst haircut you've ever had, and do photos still exist?
Why ask it
Self-directed, so nobody is teasing anyone else. The photo question is what makes it work, since it usually ends with three phones being passed around. Skip it if anybody in the group is sensitive about appearance.
Would you rather never be able to whisper or never be able to shout?
Why ask it
A better would-you-rather than the standard ones because both options are absurd and neither is grim. Watch for whoever immediately starts working out the practical consequences, which is the actual entertainment.
What's the strangest thing in your room right now?
Why ask it
Grounded in something real, which means no invented answers. It also tends to produce an offer to go and get the object, and a group that ends up looking at somebody's strange lamp is a group that is getting along.
What's the most embarrassing thing that's happened to you in public?
Why ask it
Only ask this once the room has warmed up, and let people pass. In a new group with any power imbalance, a question that asks for humiliation can stop being voluntary very quickly, so say plainly that skipping is fine.
What's the strangest dream you can actually remember?
Why ask it
Dreams are impossible to summarize, so this produces rambling and specific answers rather than polished ones. That is exactly what you want in an icebreaker, where the polished answers are the forgettable ones.
If you could have any animal as a roommate, which one and why?
Why ask it
The reasoning is where this gets good, because the practical people pick something that would help with chores and everyone else picks something enormous. It also gets pet stories out of half the room.
What's something completely irrational that you refuse to do?
Why ask it
Everyone has one: stepping on a crack, sleeping with a closet door open, a specific number. It is a confession with no cost, and the room will find at least two people who share the same one.
What's the worst movie you would happily watch again tomorrow?
Why ask it
Lets people be enthusiastic about something they know is bad, which is more revealing than asking for a favorite film. Anyone who names a genuinely respected film has misread the question, and that is worth teasing gently.
What's the most ridiculous thing you've convinced someone was true?
Why ask it
Keep it aimed at harmless nonsense told to a sibling or a roommate. If answers start heading toward anything cruel, redirect. In this setting, stories that celebrate making someone else look foolish set exactly the wrong precedent.
If you had a walk-on song that played whenever you entered a room, what would it be?
Why ask it
One of the few questions here that will actually get played out loud, which is worth doing. Choices split between songs people genuinely like and songs chosen for the bit, and both tell you something.
What's the strangest thing you've seen a stranger do in public?
Why ask it
Points outward instead of inward, which makes it a good reset after the more personal questions. Answers usually involve public transport, and somebody in the room will have witnessed something very similar.
If you could pick up any skill instantly, what would you do with it first?
Why ask it
The first thing is the real question, because the skill by itself is a boring answer. Someone who says they would learn a language and then call a specific relative has told you something a direct question never would.
How would you describe your first week here using only movie titles?
Why ask it
Shared reference point, which matters in a group of new members who are all going through the same thing. It also gives them permission to admit the first week was strange without complaining about anybody in particular.
What's something you're genuinely better at than most people?
Why ask it
A closer, and deliberately the opposite of the useless talent question. New members usually undersell here, so ask a follow-up rather than accepting a shrug. Ending on what people are good at is better than ending on embarrassment.
How to use these with new members
Practical guidance for the conversation itself
Ground rules that matter here
- These are icebreakers, not tasks. Nothing on this list should be assigned, scored, timed, or used as a condition of anything.
- Say at the start that anybody can pass on any question, and then actually let people pass without comment the first time it happens.
- Answer every question yourself before anyone else does. A room where only new members are answering is not a conversation, whatever it is called.
- No alcohol attached to answers, no forfeits, no consequences for a boring answer. Anything with a penalty attached stops being a question.
Running it in a group
- Two or three questions with everyone answering beats twenty questions with three people talking. Pick a short list and give each person room.
- Vary who goes first. Whoever answers first sets the length and tone for the whole circle, so do not let the same confident person open every round.
- Break a large group into fours. In a circle of thirty, nineteen people wait in silence and stop listening.
- Wrap up early. Ending while people still want another round is what makes them keen next time.
What to leave out
- Nothing about family money, background, religion, politics, dating history or bodies. In a group of near-strangers with an imbalance in it, none of these are neutral.
- No dares and no questions built around eating, drinking or doing something on command. That is where icebreakers turn into something else entirely.
- Do not press anyone who deflects. One skipped question is not a problem, and pushing on it in front of a room is.
- Check your chapter and university policy before running any group activity with new members, and keep whatever you run comfortably inside it.
Making the answers stick
- Follow up with why rather than moving straight to the next person. One reason remembered beats twenty answers forgotten.
- Look for overlaps out loud. Two people with the same irrational rule or the same terrible film now have something to talk about after the meeting.
- Ask for the demonstration when someone offers one, and never when they do not.
- Note down two facts about each new person afterward and use them next week. Remembering the answer is worth more than asking the question.