Sendit Questions to Ask
Prompts to post on Sendit when you want anonymous replies worth reading, from first impressions and guessing games to the more direct questions, with notes on which prompts tend to invite unkind answers and what to do if the replies turn nasty.
The questions
Open any question for the note
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 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.
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 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 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.
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'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 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.
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.
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 would you change about how I act around other people?
Why ask it
This gets genuine answers and it can sting, so decide before posting that you will not go hunting for the sender. Repeated themes are worth thinking about; one harsh reply usually says more about whoever wrote it.
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.
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.
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.
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'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.
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.
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.
Getting Replies Worth Reading
Practical guidance for the conversation itself
Choosing a Prompt
Guessing prompts get volume, open prompts get depth
Song and spending guesses are answered by people who would never write a paragraph. Open questions get fewer replies but better ones. Alternate rather than posting two of the same kind in a row.
One prompt at a time
Two questions in a single post means most people answer the easier one. If you want the honest answers, ask only for those.
Reply to a few in public
Reposting two or three answers, including one that was not flattering, is what makes people bother next time. A prompt that never gets acknowledged gets ignored the following week.
Keep it answerable in one line
Anonymous replies are typed quickly on a phone. Anything that needs a paragraph of setup gets skipped in favour of a one-word joke.
Before You Post the Blunt Ones
Decide in advance not to hunt for names
Trying to work out who sent something is where these games go wrong. Guessing wrong in public costs you a friendship, and guessing right rarely improves anything.
Assume some replies are exaggerated
Without their name attached, people overstate. Treat a criticism repeated by several senders as real information, and treat a single vicious message as one person having a bad evening.
Do not read them right before bed
The prompts about what annoys people and what they would change hit hardest late at night. Post in the afternoon and read the replies when you are not tired.
Skip the ones aimed at other people
Prompts asking for secrets about someone else, or for who is the worst in your year, turn into bullying with your name on the post. Keep the questions about you.
Staying Safe in the Replies
- Do not put your school, address, workplace or plans for the weekend into a reply you post publicly, however harmless the question that prompted it.
- Do not answer on someone else's behalf. Anonymous senders sometimes fish for information about a friend rather than about you.
- Treat anonymity as temporary. Screenshots travel, accounts get shared, and people talk, so send nothing you would not want attached to your name later.
- Blocking, reporting and turning the whole thing off are all reasonable responses to one nasty message, not overreactions.
- If replies become threatening, sexual or persistent, keep the screenshots and tell someone who can act, a parent, a teacher, or the platform's reporting tools. That is not the same as being unable to take a joke.
If You Are the One Sending
- Ask yourself whether you would send it signed. If the answer is no, that is usually a reason not to send it at all rather than a reason to stay anonymous.
- Anonymous compliments are the best thing about this format, and they cost nothing. The specific ones get remembered for years.
- If you know something is wrong with a friend, an anonymous message is a poor way to raise it. Say it in a normal conversation instead.
- Consider signing it. Half the messages people keep from these apps are the ones where the sender owned up at the end.