Questions to Ask on Sendit
Prompts to post on Sendit and other anonymous question apps, short enough to answer in one line and light enough to stay fun, with notes on which ones invite unkind replies.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
What song have you replayed the most this month?
Why ask it
Replay counts are visible in most music apps, so this one is easy to answer honestly, and the song usually opens a follow-up faster than asking about a favorite artist.
What is the funniest thing that happened to you this week?
Why ask it
Keeping it to this week makes the answer small and retrievable. Asking for the funniest thing ever puts people on the spot and usually gets nothing back.
What food would you eat every day without getting bored?
Why ask it
Food loyalty is low stakes and instantly arguable, so it pulls replies from people who ignore deeper prompts. Expect a side argument about whether cereal counts as a meal.
What is the most useless thing you are weirdly good at?
Why ask it
Framing the skill as useless gives people permission to brag without looking arrogant, which is why this gets answers when asking what someone is good at does not.
Who in our group would last longest in a horror film?
Why ask it
Casting friends into a scenario is more fun than rating them, and the reasoning is the payoff. Keep it to survival rather than looks or popularity, which is where these prompts turn mean.
What show did you finish in one sitting?
Why ask it
A single-sitting binge dates a specific weekend and usually arrives with the reason it happened. It also gives everyone reading something to try next.
What is the last photo in your camera roll?
Why ask it
The last photo is a random slice of an actual day rather than a curated answer, which is why it gets better replies than asking about a favorite picture.
What trend are you refusing to take part in?
Why ask it
Refusing a trend lets someone state a preference without insulting anyone in particular. The answers tend to show how much they care about being seen a certain way.
What is the best thing anyone has said to you?
Why ask it
Remembered compliments are often oddly small: something a coach or a stranger said years ago. What stuck says more than what people claim to value.
What would your walk-on song be?
Why ask it
This is a self-image question wearing a music question's clothes. The gap between the song they choose and how they actually behave is usually the joke.
What is your order that never changes?
Why ask it
Standing orders are specific and quick to type, which is what an anonymous prompt needs. They also give away habits, budgets, and how adventurous someone really is.
What is the most chaotic thing that has happened in a group chat you are in?
Why ask it
Everyone has one thread that went off the rails, and this asks for a story rather than a trait. It works best in a group that shares the reference.
If our friend group had assigned roles, what would mine be?
Why ask it
Being cast by other people is more interesting than picking your own label, and the replies usually come back sharper and kinder than expected. Be ready to hear something true.
What did you think was completely normal until you found out it was not?
Why ask it
Family habits people assume are universal, dinner times, nicknames, rules about shoes, produce genuinely surprising answers that nobody can prepare in advance.
What is your unpopular opinion about a film everyone loves?
Why ask it
Attaching the opinion to a film keeps the disagreement about the film rather than the person, which is how you get a debate instead of a fight.
What would you do first with an unexpected day off?
Why ask it
A free day exposes what someone is actually short of: sleep, friends, quiet, time for a project. The answers are short and often more honest than the question looks.
What do people get wrong about you at first?
Why ask it
Most people have a ready theory about their own first impression, and the answer shows which trait they think gets misread. Notice whether they blame others for the misreading.
What is the pettiest reason you have stopped replying to someone?
Why ask it
Petty grudges are funny because they are universal, and framing the cutoff as trivial keeps the answers away from real conflict.
What is one thing you want to do before the year ends?
Why ask it
A deadline makes the answer concrete rather than aspirational, and it is short enough to type. It also gives friends something to hold them to.
What is something you have not told anyone here, but would not mind sharing?
Why ask it
The escape clause is what makes this safe on an anonymous app: it invites a disclosure without pressuring anyone into one. Drop the clause and the question becomes a dare.
What was your first impression of me?
Why ask it
The default prompt, and it earns the place: almost everyone has a first impression stored, and people are far franker about it anonymously. Expect a split between those who found you intimidating and those who found you loud, which is more useful than any compliment.
What's something you think I'm good at?
Why ask it
Praise is easier to send anonymously than in person, and the replies usually name things you never counted as skills. These are the ones worth keeping for a bad week.
What's a compliment you've thought about me but never said out loud?
Why ask it
Different from asking what people like about you, because it asks specifically for the ones that were held back. Those tend to be far more specific, which is why this prompt outperforms the generic version.
What song do I remind you of?
Why ask it
Answers come back as a title rather than a paragraph, which makes this the easiest prompt to repost. The picks tend to cluster, and the cluster tells you what mood people associate with you.
Guess my most played song this year.
Why ask it
Almost no effort to answer and impossible to take badly, which makes it the prompt to post when you want volume rather than revelations. The wrong guesses are usually funnier than the right ones.
What do you think I spend most of my money on?
Why ask it
A guessing prompt, so the answers arrive as jokes with observation underneath. What people think you spend money on is a fairly accurate summary of what you talk about most.
Which of my friends do you think I'm most like?
Why ask it
Comparison to people you know well is oddly revealing, because it tells you which of your habits are visible from outside. Most people disagree with the answer and then think about it for a week.
Where do you think I'll be living in five years?
Why ask it
A prediction prompt, so the replies show how people read your ambitions. Being told you will end up somewhere you have never considered is the interesting outcome here.
What do you think I worry about most?
Why ask it
Gentler than it looks, and the replies come from whoever pays real attention. If several people name the same worry, it is considerably more visible than you assumed.
What's a nickname you have for me that I don't know about?
Why ask it
Nicknames are easy to admit anonymously and awkward to admit in person, so this collects the ones that have been circulating for months. Expect at least one you will pretend to be annoyed about.
If we bumped into each other tomorrow, what would you say first?
Why ask it
This asks for an opening line rather than a verdict, which is why quieter people answer it. It also shows you who has been waiting for a reason to start talking to you again.
What's something you'd want to do together but haven't asked about?
Why ask it
Turns the format into an invitation. Unlike most prompts here, this one can produce an actual plan, and the replies usually come from people who were hoping you would ask first.
Which of my posts made you laugh, and which made you cringe?
Why ask it
Pairing the laugh with the cringe stops the replies turning into flattery. The cringe half lands harder than people expect, so post this when you are in a good mood rather than a fragile one.
Do you think I've changed this year, and how?
Why ask it
Better than asking whether people like you, because it asks for an observation instead of a verdict. Replies often mention something you had not noticed shifting.
What's something you've always wanted to ask me but haven't?
Why ask it
Deliberately wide open, and the questions people have been sitting on are usually about your relationships or your plans. Answer two or three publicly and you will get more of them next time.
What's a rumour you've heard about me that isn't true?
Why ask it
This hands you the version of yourself that circulates out of your hearing. Anonymity genuinely helps here, since nobody wants to be identified as the one who repeated it, and knowing beats not knowing.
What's something I do that annoys you?
Why ask it
The riskiest prompt in the set. Post it only if you can read criticism without needing to know who sent it, and keep in mind that anonymity removes the usual social cost of exaggerating.
If you could tell me one thing without ever owning it, what would it be?
Why ask it
The prompt this whole format exists for, and it produces both the kindest and the cruellest messages you will receive. Post it when you have the room to sit with either.
Give me one hint about who you are.
Why ask it
Not a question about you at all, which is exactly why it works as a closer. Hints are the only currency in an anonymous exchange, and asking for one turns the whole thing into a game instead of a scoreboard.
Using anonymous question apps well
Practical guidance for the conversation itself
What anonymity does to answers
Anonymity raises honesty and cruelty together
The same cover that gets you a real answer about someone's week gets you an insult about their appearance. Prompts that ask people to rate, rank, or judge each other are the ones that turn nasty, so ask about experiences instead.
Screenshots make it permanent
Anything posted in these apps can be captured and forwarded, including your prompt. Write as though the whole group will read it next month, because some of them will.
Anonymous does not mean untraceable
Most of these apps reveal partial hints, and friends guess correctly more often than senders expect. Do not send anything you would not stand behind if the guess landed on you.
Writing prompts that get replies
- Keep it to one sentence that can be answered in five words.
- Anchor it in time: this week, this month, last summer.
- Ask for one specific thing rather than a favorite, since favorites are hard to choose on demand.
- Give an escape route in anything personal, such as if you do not mind saying.
- Post two or three a week rather than ten in an evening.
- Reply to the answers you get, or people stop bothering.
Prompts to skip
Anything about bodies or appearance
Rating looks, weight, or who is most attractive is where these apps do the most damage, and the replies are remembered long after the thread. There is no kind version of this prompt.
Requests to reveal someone else's secret
Asking who likes whom, or what someone said about a third person, hands out other people's information without consent and reliably starts arguments the sender does not have to face.
Fishing for insecurities
Questions about someone's biggest fear, worst insecurity, or most embarrassing search history look like closeness and function as pressure. Save that ground for conversations where people know who they are talking to.
If a reply is cruel
- Do not reply to it in the thread. Public responses reward the sender with attention.
- Screenshot it before deleting, in case it continues and you need a record.
- Use the app's block and report tools, and turn the question off if replies keep coming.
- Tell one person offline. Anonymous abuse works because it stays private.
- If it involves threats or anything sexual and the people involved are under age, take it to a parent, a teacher, or the platform directly rather than handling it alone.